Synthesis of enantiopure triazolium salts from pyroglutamic acid and their evaluation in the benzoin condensation

被引:111
作者
Enders, Dieter [1 ]
Han, Jianwei [1 ]
机构
[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1016/j.tetasy.2008.05.017
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A family of enantiopure 1,2,4-triazolium salts were prepared starting from the inexpensive (S)-pyroglutamic acid. After treatment with base, the corresponding N-heterocyclic carbenes were tested as organo-catalysts in the asymmetric benzoin condensation and gave good yields and up to 95% ee. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1367 / 1371
页数:5
相关论文
共 37 条
  • [21] A highly enantioselective catalytic intramolecular Stetter reaction
    Kerr, MS
    de Alaniz, JR
    Rovis, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10298 - 10299
  • [22] Comparison of chiral thiazolium and triazolium salts as asymmetric catalysts for the benzoin condensation
    Knight, RL
    Leeper, FJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (12): : 1891 - 1893
  • [23] 5-AZA-SEMICORRINS - A NEW CLASS OF BIDENTATE NITROGEN LIGANDS FOR ENANTIOSELECTIVE CATALYSIS
    LEUTENEGGER, U
    UMBRICHT, G
    FAHRNI, C
    VONMATT, P
    PFALTZ, A
    [J]. TETRAHEDRON, 1992, 48 (11) : 2143 - 2156
  • [24] Marion N., 2007, ANGEW CHEM, V119, P3046
  • [25] N-heterocyclic carbenes as organocatalysts
    Marion, Nicolas
    Diez-Gonzalez, Silvia
    Nolan, Steven P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) : 2988 - 3000
  • [26] Preparation of axially chiral N,N′-diarylimidazolium and N-arylthiazolium salts and evaluation of their catalytic potential in the benzoin and in the intramolecular stetter reactions
    Pesch, J
    Harms, K
    Bach, T
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (09) : 2025 - 2035
  • [27] Conversion of α-haloaldehydes into acylating agents by an internal redox reaction catalyzed by nucleophilic carbenes
    Reynolds, NT
    de Alaniz, JR
    Rovis, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9518 - 9519
  • [28] ROVIS T, 2008, CHEM LETT, V2
  • [29] Asymmetric organocatalysis
    Seayad, J
    List, B
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) : 719 - 724
  • [30] METHODS OF REACTIVITY UMPOLUNG
    SEEBACH, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (04): : 239 - 258