Aspartate-catalyzed asymmetric epoxidation reactions

被引：119

作者：

Peris, Gorka ^{[1
]}

Jakobsche, Charles E. ^{[1
]}

Miller, Scott J. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 28期

关键词：

D O I：

10.1021/ja073055a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report enantioselective epoxidation reactions that are catalyzed by aspartic acid-containing peptides. The strategy involves the transient conversion of the aspartate carboxylic acid side chain to the corresponding peracid. Reaction of olefin with the activated catalyst regenerates that catalyst, which may be subjected to multiple turnovers through a carbodiimide-mediated dehydration pathway. Enantioselectivities of up to 92% ee are observed for a class of urethane-substituted olefins.

引用

页码：8710 / +

页数：3

共 22 条

[1] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].