Influence of electronic and steric factors on 2,3-dihydroimidazo [1,2-a]pyridine-based enantioselective acylation catalysts

被引：44

作者：

Birman, VB ^{[1
]}

Li, XM ^{[1
]}

Jiang, H ^{[1
]}

Uffman, EW ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

基金：

美国国家卫生研究院;

关键词：

organocatalysis; non-enzymatic asymmetric acylation catalysts; enantioselective acyl transfer; kinetic resolution;

D O I：

10.1016/j.tet.2005.08.119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic activity and enantioselectivity of chiral 2,3-dihydroimidazo[1,2-a]pyridine (DHIP) derivatives was examined as a function of the steric environment of the nucleophific nitrogen and the electronic properties of the pyridine ring. 2-Phenyl-6-trifluoroinethyl-DHIP (CF3-PIP) was confirmed to be the best catalyst in this series. In addition, three second-generation catalysts derived from the 1,2dihydroimidazo[1,2-a]quinoline (DHIQ) core were tested and proved to be considerably more active than CF3-PIP. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：285 / 294

页数：10

共 39 条

[1] Kinetic resolution of alcohols using a 1,2-dihydroimidazo[1,2-a]quinoline enantioselective acylation catalyst [J].