Regiospecific ring-opening reactions of aziridines bearing an alpha,beta-unsaturated ester group with trifluoroacetic acid or methanesulfonic acid: application to the stereoselective synthesis of (E)-alkene dipeptide isosteres

被引：47

作者：

Tamamura, H

Yamashita, M

Muramatsu, H

Ohno, H

Ibuka, T

Otaka, A

Fujii, N

机构：

[1] Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku

来源：

CHEMICAL COMMUNICATIONS | 1997年 / 23期

关键词：

D O I：

10.1039/a706027k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of N-(2,4,6-trimethylphenylsulfonyl)-gamma,delta-cis- or -trans-gamma,delta-epimino (E)-alpha,beta-enoates with acids such as TFA or methanesulfonic acid (MSA) affords the stereo- and regioselective ring-opened products in high yields, and subsequent treatment of resulting delta-aminated gamma-mesyloxy alpha,beta-enoates with organocopper reagents yields diastereoisomerically pure (E)-alkene dipeptide isosteres.

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页码：2327 / 2328

页数：2

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