Synthesis of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles from 1,2-amino alcohols

被引：45

作者：

Matsuoka, Yuki ^{[1
]}

Ishida, Yasuhiro ^{[1
]}

Sasaki, Daisuke ^{[1
]}

Saigo, Kazuhiko ^{[1
]}

机构：

[1] Univ Tokyo Hongo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, Tokyo 1138656, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 34期

关键词：

1,2-amino alcohol; chiral pool; cyclocondensation; enantiopure; N-substituted imidazole;

D O I：

10.1016/j.tet.2006.05.079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly versatile method for the preparation of enantiopure 1-substituted, 1, 2-disubstituted, and 1,4,5-trisubstituted imidazoles was developed by using the cyclocondensation reaction of a 1,2-dicarbonyl compound, an aldehyde, a 1,2-amino alcohol, and ammonium acetate. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8199 / 8206

页数：8

共 59 条

[51] IMIDAZOLE NUCLEOSIDES AND NUCLEOTIDES
TOWNSEND, LB
[J]. CHEMICAL REVIEWS, 1967, 67 (05) : 533 - +
[52] Microwave-assisted synthesis of substituted imidazoles on a solid support under solvent-free conditions
Usyatinsky, AY
Khmelnitsky, YL
[J]. TETRAHEDRON LETTERS, 2000, 41 (26) : 5031 - 5034
[53] Synthesis of new chiral ionic liquids from natural acids and their applications in enantioselective Michael addition
Wang, ZM
Wang, Q
Zhang, Y
Bao, WL
[J]. TETRAHEDRON LETTERS, 2005, 46 (27) : 4657 - 4660
[54] Synthesis and properties of ionic liquids derived from the 'chiral pool'
Wasserscheid, P
Bösmann, A
Bolm, C
[J]. CHEMICAL COMMUNICATIONS, 2002, (03) : 200 - 201
[55] Wasserscheid P, 2000, ANGEW CHEM INT EDIT, V39, P3772, DOI 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO
[56] 2-5
[57] Wasserscheid P., 2003, Ionic Liquids in synthesis
[58] Room-temperature ionic liquids. Solvents for synthesis and catalysis
Welton, T
[J]. CHEMICAL REVIEWS, 1999, 99 (08) : 2071 - 2083
[59] Zhong J., 2005, NAT PROD REP, V22, P196

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