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

被引:110
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 [J].
Kerr, MS ;
de Alaniz, JR ;
Rovis, T .
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 [J].
Knight, RL ;
Leeper, FJ .
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 [J].
LEUTENEGGER, U ;
UMBRICHT, G ;
FAHRNI, C ;
VONMATT, P ;
PFALTZ, A .
TETRAHEDRON, 1992, 48 (11) :2143-2156
[24]  
Marion N., 2007, ANGEW CHEM, V119, P3046
[25]   N-heterocyclic carbenes as organocatalysts [J].
Marion, Nicolas ;
Diez-Gonzalez, Silvia ;
Nolan, Steven P. .
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 [J].
Pesch, J ;
Harms, K ;
Bach, T .
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 [J].
Reynolds, NT ;
de Alaniz, JR ;
Rovis, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9518-9519
[28]  
ROVIS T, 2008, CHEM LETT, V2
[29]   Asymmetric organocatalysis [J].
Seayad, J ;
List, B .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) :719-724
[30]   METHODS OF REACTIVITY UMPOLUNG [J].
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (04) :239-258