STERIC CONTROL OF EPOXIDATION BY CARBAMATE AND AMIDE GROUPS - EVIDENCE FOR THE CARBONYL-DIRECTED EPOXIDATION

被引:82
作者
KOCOVSKY, P [1 ]
STARY, I [1 ]
机构
[1] CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECHOSLOVAKIA
关键词
D O I
10.1021/jo00297a047
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylic and homoallylic carbamoyloxy groups show a pronounced syn stereodirecting effect on peroxy acid epoxidation similar to that of hydroxy groups (5—8). Carbonyl oxygen of the ambident carbamoyloxy group has been found to be responsible for this steering. A similar effect operates in olefinic amides (64-66). © 1990, American Chemical Society. All rights reserved.
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页码:3236 / 3243
页数:8
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