2,3-dihydroimidazo[1,2-a]pyridines: A new class of enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols

被引：184

作者：

Birman, VB ^{[1
]}

Uffman, EW ^{[1
]}

Hui, J ^{[1
]}

Li, XM ^{[1
]}

Kilbane, CJ ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 39期

关键词：

D O I：

10.1021/ja0491477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The long-known, but previously unexplored 2,3-dihydroimidazo[1,2-a]pyridine (DHIP) has been shown to be a competent acyl transfer catalyst. Its chiral 2-phenyl derivatives obtainable in two steps from commercially available starting materials have proved to be effective acylation catalysts, giving high levels of enantioselectivity (s = 20-85) in kinetic resolution of secondary benzylic alcohols. A transition state model explaining the observed selectivity has been proposed. Copyright © 2004 American Chemical Society.

引用

页码：12226 / 12227

页数：2

共 31 条

[1]

Bremer O, 1936, LIEBIGS ANN CHEM, V521, P286

[2] Mild regioselective halogenation of activated pyridines with N-bromosuccinimide [J].