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Journal Cover Tetrahedron Letters
  [SJR: 0.782]   [H-I: 145]   [126 followers]  Follow
    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 0040-4039 - ISSN (Online) 1359-8562
   Published by Elsevier Homepage  [3123 journals]
  • Guanidine organocatalysis for enantioselective carbon-heteroatom
           bond-forming reactions
    • Authors: Keisuke Hosoya; Minami Odagi; Kazuo Nagasawa
      Pages: 687 - 696
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Keisuke Hosoya, Minami Odagi, Kazuo Nagasawa
      Guanidine-containing molecules have been employed as organocatalysts, and chiral guanidines have been widely explored as catalysts for mediating asymmetric reactions by constructing an asymmetric reaction environment. Currently, many guanidine-catalyzed asymmetric reactions are available, and some excellent reviews have appeared. In this Digest, we focused on recent progress in the guanidine-catalyzed asymmetric construction of CN, CO, CP, and CS bonds, especially developments since 2010.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.058
       
  • Recent topics on catalytic transformations of aromatic molecules via
           η6-arene transition metal complexes
    • Authors: Shin Takemoto; Hiroyuki Matsuzaka
      Pages: 697 - 703
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Shin Takemoto, Hiroyuki Matsuzaka
      The π-complexation of an arene to a transition metal center delivers many useful reactivities to the arene moiety. Although synthetic methodologies that take advantage of such π-coordination have mostly been developed as stoichiometric processes, there have been considerable recent advances in the catalytic transformations of aromatic molecules through their activation in the form of transition metal η6-arene complexes. These advances include the π-coordination catalyzed transformations of aryl-heteroatom and side-chain CH and CC bonds and the palladium-catalyzed CH functionalization in pre-formed transition metal η6-arene complexes. This digest paper aims to provide a concise view of these recent advances in the area of transition metal η6-arene complexes.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.036
       
  • Total synthesis of (+)-UCS1025A based on a sequential Michael-retro
           Michael strategy featuring one-pot six-step cascade reaction
    • Authors: Ryota Sano; Ryo Kosuge; Tetsu Tsubogo; Hiromi Uchiro
      Pages: 704 - 707
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Ryota Sano, Ryo Kosuge, Tetsu Tsubogo, Hiromi Uchiro
      The asymmetric total synthesis of UCS1025A is accomplished by establishing a novel and efficient method for the construction of a tricyclic pyrrolizidinone skeleton based on a sequential Michael-retro Michael strategy. The key step is a one-pot six-step cascade reaction including oxidation of a primary alcohol to the corresponding carboxylic acid, a retro thio-Michael reaction, and an intramolecular oxy-Michael reaction. This newly-developed synthetic strategy inspired by “masked” electrophilic character of tricyclic pyrrolizidinone is efficient and high-yielding compared to that developed in previously-reported total syntheses.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.025
       
  • Syntheses of the marine alkaloids 6-oxofascaplysin, fascaplysin and their
           derivatives
    • Authors: Maxim E. Zhidkov; Alexey V. Kantemirov; Alexey V. Koisevnikov; Alexander N. Andin; Alexandra S. Kuzmich
      Pages: 708 - 711
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Maxim E. Zhidkov, Alexey V. Kantemirov, Alexey V. Koisevnikov, Alexander N. Andin, Alexandra S. Kuzmich
      A simple approach towards the pyrido[1,2-a:3,4-b′]diindole system via the reaction of indigo with methylene active compounds was used for the syntheses of the marine alkaloids 6-oxofascaplysin, fascaplysin, and their derivatives. It was also demonstrated that the reaction with ketones led to indigo decomposition and the formation of isatin derivatives. The derivative of fascaplysin with a phenyl substituent at C-7 demonstrated 2–3 times greater inhibitory activity against selected cancer cell lines than fascaplysin.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.023
       
  • On-off switching of gel formation by red-ox reaction
    • Authors: Daisuke Yakeya; Tetsuji Moriguchi; Akihiko Tsuge
      Pages: 712 - 714
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Daisuke Yakeya, Tetsuji Moriguchi, Akihiko Tsuge
      Organogelator candidates which consist of the ferrocene unit have been prepared. It has been suggested that two amino acid residues in the structure are necessary to form a stable organogel. Addition of an oxidizing agent such as NaClO induces the collapse of the gel, and reproduction of the gel was observed by addition of a reducing agent such as glutathione. It has been found out that the on-off switching of gel formation can be achieved by red-ox reaction.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.013
       
  • Accessing substituted pyrrolidines via formal [3+2] cycloaddition of
           1,3,5-triazinanes and donor-acceptor cyclopropanes
    • Authors: Zhi-Yao Chu; Na Li; Dan Liang; Zheng-Hui Li; Yong-Sheng Zheng; Ji-Kai Liu
      Pages: 715 - 718
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Zhi-Yao Chu, Na Li, Dan Liang, Zheng-Hui Li, Yong-Sheng Zheng, Ji-Kai Liu
      The formal [3+2] cycloaddition of 1,3,5-triaryl-1,3,5-triazinanes with donor-acceptor cyclopropanes has been found to provide pyrrolidines in good to excellent yields under mild reaction conditions. Preliminary mechanistic investigation indicates that this formal [3+2] cycloaddition reaction proceeds through competing SN1 and SN2 pathways.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.016
       
  • Ir-catalyzed asymmetric hydrogenation of simple ketones with chiral
           ferrocenyl P,N,N-ligands
    • Authors: Chao Qin; Chuan-Jin Hou; Hongzhu Liu; Yan-Jun Liu; De-Zhi Huang; Xiang-Ping Hu
      Pages: 719 - 722
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Chao Qin, Chuan-Jin Hou, Hongzhu Liu, Yan-Jun Liu, De-Zhi Huang, Xiang-Ping Hu
      The Ir-catalyzed asymmetric hydrogenation of simple aromatic ketones with chiral ferrocenyl P,N,N-ligands has been developed. Under the optimized conditions, a wide range of ketones were hydrogenated to afford the corresponding chiral alcohols in good to excellent enantioselectivities (up to 98% ee).
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.020
       
  • PCl3- and organometallic-free synthesis of tris(2-picolyl)phosphine oxide
           from elemental phosphorus and 2-(chloromethyl)pyridine hydrochloride
    • Authors: Svetlana F. Malysheva; Nataliya A. Belogorlova; Vladimir A. Kuimov; Yurii I. Litvintsev; Irina V. Sterkhova; Alexander I. Albanov; Nina K. Gusarova; Boris A. Trofimov
      Pages: 723 - 726
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Svetlana F. Malysheva, Nataliya A. Belogorlova, Vladimir A. Kuimov, Yurii I. Litvintsev, Irina V. Sterkhova, Alexander I. Albanov, Nina K. Gusarova, Boris A. Trofimov
      In the superbase KOH/H2O/toluene/phase-transfer catalyst system, 2-picolyl chloride, generated in situ from 2-(chloromethyl)pyridine hydrochloride, reacts with elemental phosphorus at 65–95 °C for 3 h to afford tris(2-picolyl)phosphine oxide in 50% yield. Single crystal X-ray analysis of the latter revealed one polymorph form of this tertiary phosphine oxide.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.021
       
  • N6-tert-Butoxycarbonyl derivatives of sydnone imines: Preparation and
           synthetic use
    • Authors: Ilya A. Cherepanov; Alina S. Samarskaya; Ivan A. Godovikov; Konstantin A. Lyssenko; Anastasia A. Pankratova; Valery N. Kalinin
      Pages: 727 - 729
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Ilya A. Cherepanov, Alina S. Samarskaya, Ivan A. Godovikov, Konstantin A. Lyssenko, Anastasia A. Pankratova, Valery N. Kalinin
      A highly efficient gram-scale method for the C(4)-functionalization of sydnone imine hydrochloride derivatives was developed. This new approach was realized through consecutive reactions including the preparation of a C(3)-substituted N 6-tert-butoxycarbonyl sydnone imine derivative, deprotonation with n-BuLi and reaction of the lithiated-intermediate with an electrophilic agent, and removal of the Boc protecting group.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.019
       
  • Synthesis, structure, and host-guest properties of an anthracene-based
           macrocyclic arene
    • Authors: Liping Bao; Xiaoyan Shu; Ma Yu; Dabin Hou; Lei Cui; Chunju Li
      Pages: 730 - 733
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Liping Bao, Xiaoyan Shu, Ma Yu, Dabin Hou, Lei Cui, Chunju Li
      A new anthracene-based macrocyclic host (H) was designed and synthesized. H has a molecular box-type structure with a flexible cavity. It exhibits highly strong binding affinities towards selected cationic model guests, butyl viologen (BV), dibutylammonium (DBA), and octyltrimethylammonium (OTMA). For example, the association constant of H and BV is up to (2.2 ± 0.3) × 107 M−1; it is interesting to observe host-guest charge-transfer band (and color change) and fluorescence quenching of H’s anthracene unit due to the formation of inclusion complex.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.017
       
  • Iron-catalyzed cross-dehydrogenative CN coupling of thiohydantoins with
           various amines
    • Authors: Sulochana S. Mudaliar; Anuj P. Patel; Janki J. Patel; Kishor H. Chikhalia
      Pages: 734 - 738
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Sulochana S. Mudaliar, Anuj P. Patel, Janki J. Patel, Kishor H. Chikhalia
      A novel iron-catalyzed CN bond construction method for the hetero-cross-dehydrogenative coupling (CDC) of diverse thiohydantoins with amines utilizing TBHP as the oxidant was developed. This sp3 CH amination at the carbons alpha to carbonyl groups of thiohydantoin tolerates the presence of a wide range of functional groups and provides the corresponding N-substituted amines in moderate to good yields. Various substrate scopes and optimum reaction conditions leads inside in organic synthesis.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.024
       
  • A facile method for the preparation of carbodiimides from thioureas and
           (Boc)2O
    • Authors: He Wu; Yan-Fang Sun; Chen Zhang; Chun-Bao Miao; Hai-Tao Yang
      Pages: 739 - 742
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): He Wu, Yan-Fang Sun, Chen Zhang, Chun-Bao Miao, Hai-Tao Yang
      A concise method for the preparation of carbodiimides from thioureas using di-tert-butyl dicarbonate [(Boc)2O] as the dehydrosulfurizative reagent has been developed. Using DMAP as the catalyst, a variety of symmetric and asymmetric 1,3-diaryl thioureas were converted into the corresponding carbodiimides efficiently in a short time.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.025
       
  • Lobarioid A, unusual antibacterial depsidone possessing an eight-membered
           diether ring from the edible lichen Lobaria sp.
    • Authors: Yu Zheng; Chao-Jiang Xiao; Kai Guo; Ying Wang; Yan Liu; Shi-Hong Luo; Xiao-Nian Li; Sheng-Hong Li
      Pages: 743 - 746
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Yu Zheng, Chao-Jiang Xiao, Kai Guo, Ying Wang, Yan Liu, Shi-Hong Luo, Xiao-Nian Li, Sheng-Hong Li
      Lobarioid A (1), an unusual depsidone possessing an eight-membered diether ring, was isolated from the edible lichen Lobaria sp. Its structure was elucidated by extensive NMR, MS, IR and single-crystal X-ray diffraction analyses. Compound 1 exhibited antibacterial activity against three strains of gram-positive bacteria.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.027
       
  • Novel tricyclic diamines 1. Synthesis of 1,4-diazaisotwistane and
           1,4-diazahomoisotwistane as constrained 3-aminoquinuclidine isosteres
    • Authors: Ivar M. McDonald; Alicia Ng; Jingfang Cutrone; Robert Mate; Richard E. Olson
      Pages: 747 - 750
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Ivar M. McDonald, Alicia Ng, Jingfang Cutrone, Robert Mate, Richard E. Olson
      Synthesis of the novel tricyclic diamines 1,4-diazaisotwistane and 1,4-diazahomoisotwistane are described. These compact tricyclic cores have one tertiary and one secondary amine and may serve as ring-constrained isosteres of 3-aminoquinuclidine. Both tricycles were prepared by a similar strategy involving saturation of an appropriately substituted aromatic azaindole, functionalization and intramolecular alkylation.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.032
       
  • Novel tricyclic diamines 2. Synthesis of 1,7-diazaisoadamantane,
           1,5-diazaisoadamantane and 1,6-diazahomobrendane
    • Authors: Ivar M. McDonald; Robert Mate; Alicia Ng; Hyunsoo Park; Richard E. Olson
      Pages: 751 - 754
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Ivar M. McDonald, Robert Mate, Alicia Ng, Hyunsoo Park, Richard E. Olson
      Three novel tricyclic diamines (1,7-diazaisoadamantane, 1,5-diazaisoadamantane and 1,6-diazahomobrendane) were prepared. A flexible synthetic strategy was employed which used flat, aromatic azaindoles as the starting materials. The requisite azaindoles were prepared by a tandem Sonogashira coupling/intramolecular cyclization reaction. Ring saturation, appropriate functionalization and intramolecular alkylation provided the three novel tricyclic diamines cores.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.028
       
  • Novel tricyclic diamines 3. Synthesis of 1,4-diazaadamantane
    • Authors: Ivar M. McDonald; Alicia Ng
      Pages: 755 - 759
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Ivar M. McDonald, Alicia Ng
      Synthesis of the previously unreported 1,4-diazaadamantane is described. The overall strategy involves complete saturation of a flat, aromatic heterocycle, appropriate functionalization and intramolecular double alkylation. The alkylation takes place via an iminophosphorane under anhydrous conditions, which produced superior results vs. alkylation of the corresponding primary amine.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.031
       
  • Enantioselective formal synthesis of (−)-aurantioclavine using
           Pd-catalyzed cascade cyclization and organocatalytic asymmetric
           aziridination
    • Authors: Shun-ichi Nakano; Yasumasa Hamada; Tetsuhiro Nemoto
      Pages: 760 - 762
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Shun-ichi Nakano, Yasumasa Hamada, Tetsuhiro Nemoto
      The enantioselective formal synthesis of (−)-aurantioclavine is described. The core tricyclic skeleton was synthesized using a Pd-catalyzed Heck insertion–allylic amination cascade. The stereocenter was constructed by a highly enantioselective organocatalytic asymmetric aziridination reaction.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.033
       
  • Convergent total synthesis of (−)-dactylolide
    • Authors: Tokihiro Tanaka; Yuto Murai; Takayuki Kishi; Hiroyoshi Takamura; Isao Kadota
      Pages: 763 - 766
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Tokihiro Tanaka, Yuto Murai, Takayuki Kishi, Hiroyoshi Takamura, Isao Kadota
      A convergent total synthesis of (−)-dactylolide is described. Constructing the 2,6-disubstituted exo-methylene THP moiety was achieved by the intramolecular allylation of α-acetoxy ether. The cyclization precursor was prepared from two segments, an alcohol and carboxylic acid derivatives, by esterification followed by reductive acetylation.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.034
       
  • Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated
           decarboxylation–cyclization of hydrazides and diketones
    • Authors: Pinhui Diao; Yanqin Ge; Wenpei zhang; Chen Xu; Nannan Zhang; Cheng Guo
      Pages: 767 - 770
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Pinhui Diao, Yanqin Ge, Wenpei zhang, Chen Xu, Nannan Zhang, Cheng Guo
      A visible-light-induced synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from simple diketones and hydrazides with the assistant of the photocatalyst eosin Y catalyzed decarboxylation and cyclization under mild conditions has been discovered. The reaction tolerates a wide range of functional groups and gives a variety of valuable 1,3,4-oxadiazoles in moderate to good yields. Finally, a plausible reaction mechanism was proposed.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.037
       
  • Synthesis of arylated chalcone derivatives via palladium cross-coupling
           reactions
    • Authors: Rafaela G.M. da Costa; Francisco R.L. Farias; Davi Back; Jones Limberger
      Pages: 771 - 775
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Rafaela G.M. da Costa, Francisco R.L. Farias, Davi Back, Jones Limberger
      A useful protocol for arylation of the olefin double bond of chalcones to afford tri- and tetra-substituted chalcone derivatives is reported. The protocol begins with the Heck reaction between chalcones and aryl iodides providing β-arylchalcones. This reaction tolerates various functional groups on both rings, as well as deactivated aryl iodides. The products are obtained in moderate to excellent yields and the (E)-β-arylchalcones (E:Z > 96:4) can be isolated via precipitation. Competitive Heck reactions pointed to a significant effect of ring one substituents on the reaction rate, while substituents on ring two have a much smaller effect. To access α,β-diarylchalcones, a sequential bromination-Suzuki cross coupling strategy was applied to the β-arylated compounds which afforded double arylated chalcone derivatives in 60–99% yield over two steps.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.038
       
  • Synthesis of polyfunctionalized pyrroles bearing C-2 α-azido side-chains
           and displacement of the α-azido group by various nucleophiles
    • Authors: Naomi Kishii; Morie Shimadu; Shun Maruyama; Sayuri Tou; Ikuo Sasaki; Hideyuki Sugimura
      Pages: 776 - 780
      Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8
      Author(s): Naomi Kishii, Morie Shimadu, Shun Maruyama, Sayuri Tou, Ikuo Sasaki, Hideyuki Sugimura
      Tetrasubstituted pyrroles bearing C-2 α-azido side-chains were synthesized employing a new class of diazides, α,γ-diazido α,β-unsaturated esters, and 1,3-dicarbonyl compounds under simple thermal conditions. Further investigation of the synthetic utility of the obtained pyrroles reveals unexpected displacement of the α-azido group at the C-2 side-chain by a variety of nucleophiles. This two-step process exhibits a broad substrate scope, good functional group tolerance, simple operation, and high reaction efficiency, providing an easy access to polyfunctional pyrroles with novel substitution patterns.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.049
       
  • Synthesis of the sedum and related alkaloids: A personal perspective
    • Authors: Roderick W. Bates
      Pages: 559 - 567
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Roderick W. Bates
      Significant recent contributions to the synthesis of the sedum alkaloids are discussed. Related compounds, such as pinidinol, porantheridine, dumetorine and the tetraponerines are also included. The syntheses are categorised according to the key motif or chemistry employed: isoxazolidines, metathesis, asymmetric aza-Michael, heterocycle lithiation, organocatalysis, aromatic heterocycles and chiral imines.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.026
       
  • Recent topics of the natural product synthesis by
           Horner–Wadsworth–Emmons reaction
    • Authors: Kenichi Kobayashi; Kosaku Tanaka; Hiroshi Kogen
      Pages: 568 - 582
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Kenichi Kobayashi, Kosaku Tanaka, Hiroshi Kogen
      The Horner–Wadsworth–Emmons (HWE) reaction has become well established among existing methodologies for the highly stereoselective olefination of carbonyl compounds. The reliability of this reaction in terms of its robustness, high stereoselectivity, and broad substrate scope permit retrosynthetic disconnection of the olefin bond in α,β-unsaturated carbonyl intermediates in natural product synthesis. This review discusses recent applications of the HWE reaction in natural product synthesis, highlighting its use for carbon chain elongation, coupling reactions of synthetic segments, ring-closing reactions, tandem reactions including HWE olefination, and asymmetric reactions.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.076
       
  • Recent advances on nonenzymatic catalytic kinetic resolution of diols
    • Authors: Hui Yang; Wen-Hua Zheng
      Pages: 583 - 591
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Hui Yang, Wen-Hua Zheng
      As one of the most efficient and straight-forward strategies for obtaining optically pure compounds, catalytic kinetic resolution has been widely used in laboratory and industry. Although nonenzymatic catalytic kinetic resolution of secondary alcohol has been well developed, it still remains a formidable challenge for kinetic resolution of diols which play a significant role in natural products synthesis. The purpose of this digest is to present the recent progress on nonenzymatic catalytic kinetic resolution of representative diols.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.080
       
  • Recent advances of hexaazatriphenylene (HAT) derivatives: Their
           applications in self-assembly and porous organic materials
    • Authors: Xiao-Yang Yan; Meng-Di Lin; Si-Tai Zheng; Tian-Guang Zhan; Xiang Zhang; Kang-Da Zhang; Xin Zhao
      Pages: 592 - 604
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Xiao-Yang Yan, Meng-Di Lin, Si-Tai Zheng, Tian-Guang Zhan, Xiang Zhang, Kang-Da Zhang, Xin Zhao
      As a rigid and planar aza-based heteroaromatic scaffold, hexaazatriphenylene (HAT) exhibits excellent electron-deficient property and high π-π stacking tendency, which makes it an ideal building block in the construction of supramolecular architectures and functional materials. In addition, HATs have also been picked out as building blocks for the construction of novel porous organic polymers, one of the most attractive fields of porous materials in the past decade, which includes intrinsic microporosity (PIMs), π-conjugated microporous polymers (CMPs), and covalent organic frameworks (COFs). In this digest paper, the synthetic methods of HAT derivatives have been briefly introduced and some recent advances of HATs in the applications of supramolecular self-assembly and porous organic materials have been highlighted.
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      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.004
       
  • Facile synthesis of isomerically pure fullerenols C60(OH)5Br and
           1,4-C60(OH)2 from chlorofullerene C60Cl6
    • Authors: Olga A. Kraevaya; Alexander S. Peregudov; Vyacheslav M. Martynenko; Pavel A. Troshin
      Pages: 605 - 607
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Olga A. Kraevaya, Alexander S. Peregudov, Vyacheslav M. Martynenko, Pavel A. Troshin
      The chlorofullerene C60Cl6 was demonstrated as a versatile precursor for the synthesis of two isomerically pure fullerenols via tetrabutylammonium bromide promoted reactions with water. Performing the synthesis in wet chlorobenzene produced 1,4-C60(OH)2 as the only isolable product along with substantial amounts of non-functionalized C60. However, the addition of DMSO as a co-solvent altered the reaction pathway, leading to the formation of C60(OH)5Br as the main product. Both isolated compounds were novel and their molecular compositions and structures were confirmed by mass spectrometry and NMR spectroscopy. The fullerenol C60(OH)5Br, which was formed in a moderate yield, represents the first isomerically pure polyhydroxylated fullerene available on a large scale.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.10.054
       
  • Synthesis of chlorinated fullerenes C60Cln (n = 2, 4) from C60Cl6 and
           their Arbuzov-type reaction with P(OEt)3
    • Authors: Alexander V. Zhilenkov; Alexander S. Peregudov; Alexander V. Chernyak; Vyacheslav M. Martynenko; Pavel A. Troshin
      Pages: 608 - 611
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Alexander V. Zhilenkov, Alexander S. Peregudov, Alexander V. Chernyak, Vyacheslav M. Martynenko, Pavel A. Troshin
      Reduction of C60Cl6 with triphenylphosphine was demonstrated to be a useful method for the preparation of a mixture of low-chlorinated fullerenes C60Cln (n = 2, 4). Individual chlorofullerene 1,4-C60Cl2 was isolated by preparative gel permeation chromatography and characterized spectroscopically for the first time. The Arbuzov-type reaction of C60Cln with P(OEt)3 produced C60[PO(OEt)2]3H as a major isolable product, which was further hydrolyzed to C60[PO(OH)2]3H.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.11.047
       
  • Synthesis of oxindoles via Cu-mediated reactions between
           N-phenylacrylamides and ethyl 2-bromo-2-methylpropionate
    • Authors: Da Liu; Shaobo Zhuang; Xiang Chen; Lin Yu; Yongqi Yu; Liang Hu; Ze Tan
      Pages: 612 - 616
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Da Liu, Shaobo Zhuang, Xiang Chen, Lin Yu, Yongqi Yu, Liang Hu, Ze Tan
      A novel way of synthesizing alkylated oxindoles via Cu-mediated atom transfer radical addition reaction between N-phenylacrylamides and ethyl 2-bromo-2-methylpropionate has been described. It was found that the use of N,N,N′,N′-1,1,2,2,-tetramethylethylenediamine as ligand was important for achieving good yields. Additionally, the use of DMSO as solvent and running the reaction at 130 °C were also crucial. In some cases, the product can be further brominated when the reaction temperature was raised to 150 °C.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.053
       
  • Practical synthesis of two novel series of 1,3-disubstituted
           β-carboline derivatives
    • Authors: Péter Ábrányi-Balogh; Balázs Volk; Mátyás Milen
      Pages: 617 - 619
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Péter Ábrányi-Balogh, Balázs Volk, Mátyás Milen
      The synthesis of two novel series of 1,3-disubstituted β-carbolines from 1-aryl-β-carboline-3-carbaldehyde building blocks is reported. In the first case, an efficient synthesis of 1-aryl-β-carboline C-3 tethered tetrahydro-imidazopyridines and their aromatic counterparts was developed. In the second case, the Willgerodt-Kindler three-component reaction was used for the transformation of aldehydes into the corresponding thioamides.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.063
       
  • Pyridone alkaloids from the scale-insect pathogenic fungus Hypocrella
           discoidea BCC 71382
    • Authors: Masahiko Isaka; Rachada Haritakun; Suchada Mongkolsamrit; Sumalee Supothina; Tao Feng; Ji-Kai Liu
      Pages: 620 - 623
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Masahiko Isaka, Rachada Haritakun, Suchada Mongkolsamrit, Sumalee Supothina, Tao Feng, Ji-Kai Liu
      Hypocrellutins A–C (1–3), 2- and 4-pyridone alkaloids, were isolated from cultures of the scale-insect pathogenic fungus Hypocrella discoidea BCC 71382. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The absolute configuration of hypocrellutin B (2) was determined by ECD calculation. Their plausibly biosynthetic pathways are proposed. All isolated compounds were inactive in the antifungal, antimalarial, antitubercular, and cytotoxic activity assays.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.084
       
  • Synthetic studies towards lagunamide C: Polyketide assembly investigations
    • Authors: Anthony Fatino; Chelsea Weese; Salvador Valdez; Alberto Jiménez-Somarribas; Ryan J. Rafferty
      Pages: 624 - 627
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Anthony Fatino, Chelsea Weese, Salvador Valdez, Alberto Jiménez-Somarribas, Ryan J. Rafferty
      Lagunamide C is a depsipeptide natural product with low nM cytotoxicity towards numerous cancer cell lines. Synthetically, it is disconnected to a pentapeptide backbone and polyketide unit that possesses four stereogenic centers, of which two of centers are in question (C38 & 40). Our model system highlights a high-selective aldol addition via a Crimmin’s auxiliary setting the C40 ester linkage, and a non-facially selective cyclopropanation with subsequent ring opening for the installation of the C38 methyl center.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.083
       
  • Mn(OAc)3*2H2O promoted addition of arylboronic acids to quinoxalin-2-ones
    • Authors: Boora Ramesh; C. Ravikumar Reddy; G. Ravi Kumar; B.V. Subba Reddy
      Pages: 628 - 631
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Boora Ramesh, C. Ravikumar Reddy, G. Ravi Kumar, B.V. Subba Reddy
      A simple method has been developed for the synthesis of 3-aryl quinoxalin-2-one derivatives through an oxidative cross-coupling of arylboronic acids with quinoxalin-2-ones using a readily available oxidant Mn(III) acetate dihydrate. This method provides 3-aryl quinoxalin-2-one scaffolds with a broad substrate scope.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2017.12.085
       
  • A novel 10-membered macrocyclic lactone from the mangrove-derived
           endophytic fungus Annulohypoxylon sp.
    • Authors: Yang Liu; Tibor Kurtán; Attila Mándi; Horst Weber; Changyun Wang; Rudolf Hartmann; Wenhan Lin; Georgios Daletos; Peter Proksch
      Pages: 632 - 636
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Yang Liu, Tibor Kurtán, Attila Mándi, Horst Weber, Changyun Wang, Rudolf Hartmann, Wenhan Lin, Georgios Daletos, Peter Proksch
      A novel 10-membered macrolactone, hypoxylide (1), was isolated from the endophytic fungus Annulohypoxylon sp. that was obtained from the Mangrove plant Rhizophora racemosa. The structure and absolute configuration of 1 were unambiguously elucidated by comprehensive 1D and 2D NMR, as well as by HRESIMS and ECD spectroscopic analyses. Hypoxylide (1) features an unprecedented polyketide skeleton comprised of a trihydroxynaphthalene-dione moiety fused to a decalactone ring. A plausible biosynthetic pathway of this novel metabolite is proposed.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.001
       
  • TBN as a metal-free reagent initiated sp3 C–H functionalization of
           glycine esters: Synthesis of quinoline-2-carboxylate esters
    • Authors: Xiaofei Liu; Yu Shao; Pengfei Li; Honghe Ji; Yu Yuan; Xiaodong Jia
      Pages: 637 - 640
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Xiaofei Liu, Yu Shao, Pengfei Li, Honghe Ji, Yu Yuan, Xiaodong Jia
      As a metal-free reagent, tert-butylnitrite (TBN) initiated aerobic sp3 C–H bond oxidation of glycine esters was achieved, providing a series of quinoline-2-carboxylates in good yields. The mechanistic investigation revealed that in the presence of molecular oxygen, TBN derived radicals were involved in the C–H bond oxidation and the terminal aromatization.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.003
       
  • Synthesis and characterization of novel push-pull oligomer based on
           naphthodithiophene-benzothiodiazole for OFETs application
    • Authors: Kai Zhang; Ji Zhang; Xiaoqin Zhang; Gui Yu; Man Shing Wong
      Pages: 641 - 644
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Kai Zhang, Ji Zhang, Xiaoqin Zhang, Gui Yu, Man Shing Wong
      A novel push-pull oligomeric semiconductor, ENBT based on naphthodithiophene-benzothiodiazole was successfully designed and synthesized. ENBT was fully characterized by 1H NMR, MS, thermogravimetric analysis (TGA), UV–vis spectra, and cyclic voltammetry (CV). Furthermore, ENBT-based OFETs were fabricated by solution-processed dip-coating technique and its charge transporting property was investigated. The film of ENBT exhibited a hole mobility as high as 1.4 × 10−2 cm2/(Vs) with a current on/off ratio of 106–107 after annealed at 160 °C. In order to give an insight to the transporting property of ENBT films, thin film morphologies after annealing at different temperatures were also studied by atomic force microscopy (AFM).
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.005
       
  • Diastereoselective carbenes: Stereoelectronic control of bent singlet
           trans-2′-substituted cyclobutylcarbenes
    • Authors: Murray G. Rosenberg; Udo H. Brinker
      Pages: 645 - 649
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Murray G. Rosenberg, Udo H. Brinker
      The UM06-2X/aug-cc-pVTZ//UM06-2X/6-311G(d) theoretical models of representative singlet trans-2′-substituted cyclobutylcarbenes were computed. The :CH-group of carbenes with an ERG is bent toward the c-C4H7-ring’s proximal C1′–C2′ single bond. The :CH-group of carbenes with an EWG is bent toward the c-C4H7-ring’s distal C1′–C4′ single bond. The contrasting stereoelectronic effect was computationally tested using trimethylsilyl vs. bromo substituents to determine if exo-1- and exo-2-substituted bicyclo[2.1.0]pentanes would be produced in diastereomeric excess.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.006
       
  • One-pot synthesis of 1-monosubstituted-1, 2, 3-triazoles from
           2-methyl-3-butyn-2-ol
    • Authors: Yaowen Liu; Chunmei Han; Xinyuan Ma; Jianhua Yang; Xuepu Feng; Yubo Jiang
      Pages: 650 - 653
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Yaowen Liu, Chunmei Han, Xinyuan Ma, Jianhua Yang, Xuepu Feng, Yubo Jiang
      An efficient method for the synthesis of 1-monosubstituted-1, 2, 3-triazoles from 2-methyl-3-butyn-2-ol under copper catalyst conditions has been developed through a one-step one-pot sequence. This method provides a concise and efficient pathway to synthesize 1-monosubstituted-1, 2, 3-triazole derivatives in good to excellent yields.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.012
       
  • Site selective [bmIm]OH catalyzed CC bond functionalization under green
           conditions
    • Authors: Khursheed Ansari; Ali Mohd Lone; Wajaht Amin Shah; Jagdamba Singh; I.R. Siddiqui
      Pages: 654 - 657
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Khursheed Ansari, Ali Mohd Lone, Wajaht Amin Shah, Jagdamba Singh, I.R. Siddiqui
      Effective methodology that activates selectively either end of a carbon–carbon triple bond requires key challenge of differentiating between the multitude of CC bonds present in complex organic molecule. The synthetic strategy exploited the electronic biases within the substrate and successfully achieved site–selective [bmIm]OH catalyzed CC bond functionalization under mild reaction conditions. This resulted in C-2-selective addition of phenacyl bromide on p-substituted phenyl acetylene and C-1 selective addition on the o-substituted phenyl acetylene leading to CC bond formation. The reaction proceeded smoothly with excellent yield under ambient conditions. This report demonstrates the progress on the catalytic activity of recyclable [bmIm]OH for selective CC bond formation.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.010
       
  • Visible light mediated aerobic photocatalytic activation of CH bond by
           riboflavin tetraacetate and N-hydroxysuccinimide
    • Authors: Guo Tang; Zhiyu Gong; Wenjun Han; Xiaoling Sun
      Pages: 658 - 662
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Guo Tang, Zhiyu Gong, Wenjun Han, Xiaoling Sun
      A green and highly efficient cooperative photocatalytic system which consists of riboflavin tetraacetate (RFT), N-hydroxysuccinimide (NHS) and FeCl3·6H2O has been developed for CH bond oxygenation with visible light under mild reaction conditions. Compared to the previous procedures about CH bond activation by using flavins as photocatalyst, we use cheap ferric chloride and NHS instead of expensive scandium triflate or biomimetic non-heme iron complex, further expand the substrate scopes. In addition, a possible radical mechanism for the CH bond oxygenation in this photocatalytic system is proposed.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.011
       
  • Daucus carota root enzyme catalyzed Henry reaction: A green approach
    • Authors: Chiranjit Acharya; Anushree Achari; Parasuraman Jaisankar
      Pages: 663 - 666
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Chiranjit Acharya, Anushree Achari, Parasuraman Jaisankar
      Enzyme from Daucus carota root catalyzed Henry reaction of substituted benzaldehydes and nitromethane in phosphate buffer of pH 7 at 28 °C to afford β-nitroalcohols in excellent yields (up to 94%).
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.009
       
  • Iron(III)-catalyzed synthesis of 3-aroylimidazo[1,2-a]pyridines from
           2-aminopyridines and ynals
    • Authors: Zhengwang Chen; Botao Liu; Pei Liang; Zhixiong Yang; Min Ye
      Pages: 667 - 670
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Zhengwang Chen, Botao Liu, Pei Liang, Zhixiong Yang, Min Ye
      An efficient iron-catalyzed intermolecular aminooxygenation of 2-aminopyridines with a wide range of ynals has been developed. 3-Aroylimidazo[1,2-a]pyridines containing various functional groups are synthesized under the standard conditions. The transformation is conducted in simple conditions and forms products in good yields.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.018
       
  • Transition-metal-free synthesis of aromatic amines via the reaction of
           benzynes with isocyanates
    • Authors: Jeong Hoon Seo; Haye Min Ko
      Pages: 671 - 674
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Jeong Hoon Seo, Haye Min Ko
      An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the NC bond in isocyanates, reacted with aryne precursors to afford various aniline derivatives in moderate to excellent yield and tolerated various substituents on the o-silyl aryl triflate and the isocyanate.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.022
       
  • PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and
           efficient synthesis of N-acetyl-2-substituted indoles
    • Authors: Nattawadee Chaisan; Wilailak Kaewsri; Charnsak Thongsornkleeb; Jumreang Tummatorn; Somsak Ruchirawat
      Pages: 675 - 680
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Nattawadee Chaisan, Wilailak Kaewsri, Charnsak Thongsornkleeb, Jumreang Tummatorn, Somsak Ruchirawat
      An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.014
       
  • Novel π-conjugated molecules based on diimidazopyridine: Significantly
           improved the photophysical, thermal and electrochemical properties bearing
           different aryl substituents
    • Authors: Xin Huang; Jinchang Tian; Feng Xu; Xiaochong Liu; Yuqin Li; Yanyan Guo; Wenyi Chu; Zhizhong Sun
      Pages: 681 - 686
      Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7
      Author(s): Xin Huang, Jinchang Tian, Feng Xu, Xiaochong Liu, Yuqin Li, Yanyan Guo, Wenyi Chu, Zhizhong Sun
      A series of π-conjugated molecules based on diimidazolepyridine derivatives were designed, synthesized by Suzuki coupling reaction and cyclization reaction and characterized. Diimidazolepyridine motif as the main structure could improve the thermal stability and optical property of the materials. All of the target compounds exhibited good thermal stabilities with Td values in the range of 416–490 °C. These compounds showed steady blue light emissions in the range of 424–478 nm and high quantum yields (0.33–0.69) in solution. Especially, compound 4f achieved appropriate energy gap (Eg = 2.69 eV) and high fluorescence quantum yields (Φf = 0.69) because of introducing electron-donating group, such energy gap was helpful to electronic transfer and transport. The materials have great potential for good electronic-transmission materials in OLEDs.
      Graphical abstract image

      PubDate: 2018-02-05T02:49:08Z
      DOI: 10.1016/j.tetlet.2018.01.015
       
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    • Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8


      PubDate: 2018-02-05T02:49:08Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8


      PubDate: 2018-02-05T02:49:08Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 21 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 8


      PubDate: 2018-02-05T02:49:08Z
       
  • Graphical abstract TOC continued
    • Abstract: Publication date: 14 February 2018
      Source:Tetrahedron Letters, Volume 59, Issue 7


      PubDate: 2018-02-05T02:49:08Z
       
 
 
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