1,2-ASYMMETRIC INDUCTION IN THE SN2'-ALLYLATION OF ORGANOCOPPER AND ORGANOZINC REAGENTS

被引：43

作者：

ARAI, M ^{[1
]}

KAWASUJI, T ^{[1
]}

NAKAMURA, E ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT CHEM,MEGURO KU,TOKYO 152,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 19期

关键词：

D O I：

10.1021/jo00071a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The S(N)2'-selective reaction of organocopper or organozinc reagents with allylic chlorides having a chiral center at the delta-position proceeds with up to 100% diastereoselectivity. The observed 1,2-asymmetric induction conforms to pure steric control (Cram-Felkin-Anh model) even in cases where conventional chelation control may seem to operate, and the level of the selectivity was found to be much higher than those found for the additions of organometallics to structurally comparable alpha-substituted carbonyl compounds.

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页码：5121 / 5129

页数：9

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