Effects of Methyl Substituents on the Activity and Enantioselectivity of Homobenzotetramisole-Based Catalysts in the Kinetic Resolution of Alcohols

被引:64
作者
Zhang, Yuhua [1 ]
Birman, Vladimir B. [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
关键词
acylation; catalyst design; kinetic resolution; organocatalysis; MANNICH REACTION; ORGANIC-SYNTHESIS; ACYLATION; BENZOTETRAMISOLE; DERIVATIVES; ALDEHYDES; IMINES; ESTERS;
D O I
10.1002/adsc.200900383
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Substitution of the tetrahydropyrimidine ring in the enantioselective acyl transfer catalyst homobenzotetramisole (HBTM) 6 with methyl groups exerts a dramatic influence on its performance in the kinetic resolution of secondary alcohols. The syn-3-methyl analogue of HBTM (9a) has proved to be superior to the parent compound in terms of catalytic activity, enantioselectivity, and synthetic accessibility.
引用
收藏
页码:2525 / 2529
页数:5
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