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
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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