Kinetic Resolution of β-Lactams via Enantioselective N-Acylation

被引:31
|
作者
Yang, Xing [1 ]
Bumbu, Valentina D. [1 ]
Birman, Vladimir B. [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
基金
美国国家科学基金会;
关键词
ACYL TRANSFER; NONENZYMATIC ACYLATION; AMINO-ACIDS; BINDING APPROACH; ALCOHOLS; CATALYST; BENZOTETRAMISOLE; DERIVATIVES;
D O I
10.1021/ol201911z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective N-acylation of 4-aryl-beta-lactams in the presence of acyl transfer catalyst CI-PIQ provides an effective method for their nonenzymatic kinetic resolution.
引用
收藏
页码:4755 / 4757
页数:3
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