SYN-S(N)2' PATHWAY IN THE REACTION OF CERTAIN GAMMA-(MESYLOXY) ALPHA, BETA-ENOATES WITH RCU(CN)MGX.BF3 REAGENTS - IMPORTANCE OF MGX AND BULKY R-GROUP UPON THE DIASTEREOSELECTIVITY

被引：47

作者：

IBUKA, T ^{[1
]}

TAGA, T ^{[1
]}

HABASHITA, H ^{[1
]}

NAKAI, K ^{[1
]}

TAMAMURA, H ^{[1
]}

FUJII, N ^{[1
]}

CHOUNAN, Y ^{[1
]}

NEMOTO, H ^{[1
]}

YAMAMOTO, Y ^{[1
]}

机构：

[1] TOHOKU UNIV,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

关键词：

D O I：

10.1021/jo00057a038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.

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页码：1207 / 1214

页数：8

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