STEREOSELECTIVE EPOXIDATION OF PHE-GLY AND PHE-PHE VINYL ISOSTERES

被引：139

作者：

JENMALM, A

BERTS, W

LI, YL

LUTHMAN, K

CSOREGH, I

HACKSELL, U

机构：

[1] UNIV UPPSALA,CTR BIOMED,DEPT ORGAN PHARMACEUT CHEM,S-75123 UPPSALA,SWEDEN

[2] UNIV STOCKHOLM,DEPT STRUCT CHEM,ARRHENIUS LAB,S-10691 STOCKHOLM,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 05期

关键词：

D O I：

10.1021/jo00084a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel Phe-Gly and Phe-Phe isosteres have been synthesized. Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid). Observed stereoselectivities of epoxidation appear to emanate from a cooperative coordination of the incoming peracid by the carbamate group and the more weakly coordinating allylic ester function.

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页码：1139 / 1148

页数：10

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