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
收藏
页码：285 / 294
页数：10
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