Carbocyclisation of zinc enolates onto unactivated double bonds: a mechanistic point of view

被引：3

作者：

Sliwinski, T ^{[1
]}

Prian, F ^{[1
]}

Denes, F ^{[1
]}

Chemla, F ^{[1
]}

Normant, JF ^{[1
]}

机构：

[1] Univ Paris 06, Chim Organ Lab, F-75252 Paris 05, France

来源：

COMPTES RENDUS CHIMIE | 2003年 / 6卷 / 01期

关键词：

carbocyclisation; carbometalation; cyclopentanes; enolates; piperidines; pyrrolidines; Reformatsky reagents;

D O I：

10.1016/S1631-0748(03)00017-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The recent results concerning the carbocyclisation reaction of zinc enolates onto an unactivated double bond are summarized, particularly on the stereochemical point of view. The implications of the observed stereochemistries on the mechanism of the reaction (O-centred zinc enolate vs C-centred zinc enolate) are discussed. Some new results leading stereoselectively to 1-amino-1-carbomethoxy-2-methyl cyclopentanes are reported, as well as the consequences of the observed stereochemistry as a strong evidence for a C-centred zinc enolate intermediate.

引用

页码：67 / 78

页数：12

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