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

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 11期

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

页码：1367 / 1371

页数：5

共 37 条

[1] TRANSFER OF ALKOXYCARBONYL FROM ALKYL IMIDAZOLIUM-2-CARBOXYLATES TO BENZYL ALCOHOL, A CYCLOHEXANONE ENAMINE AND DIETHYLAMINE
BAKHTIAR, C
SMITH, EH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (03): : 239 - 243
[2] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones
Burstein, C
Glorius, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6205 - 6208
[3] Burstein C., 2004, ANGEW CHEM, V116, P6331
[4] Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes
Chow, KYK
Bode, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) : 8126 - 8127
[5] New developments in the asymmetric Stetter reaction
Christmann, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) : 2632 - 2634
[6] Christmann M., 2005, ANGEW CHEM, V117, P2688
[7] Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis
Enders, D
Niemeier, O
Balensiefer, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) : 1463 - 1467
[8] Nucleophilic carbenes in asymmetric organocatalysis
Enders, D
Balensiefer, T
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 534 - 541
[9] Enders D, 2002, ANGEW CHEM INT EDIT, V41, P1743, DOI 10.1002/1521-3773(20020517)41:10<1743::AID-ANIE1743>3.0.CO
[10] 2-Q

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