Preparation of enolate-homoenolate species as (Z)-γ-siloxyallylmetal equivalents:: Sequential 1,4-addition of bis(iodozincio)methane to 1,4-dicarbonylbutenes and cyclopropanation

被引：21

作者：

Hirayama, T ^{[1
]}

Oshima, K ^{[1
]}

Matsubara, S ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo, Kyoto 6158501, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 21期

关键词：

allylic compounds; amino alcohols; cyclization; diastereoselectivity; zinc;

D O I：

10.1002/anie.200500133

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Enolate-homoenolate equivalents 1 can be prepared in one step by the title reaction. They act as functionalized Z-γ-siloxyallyl zinc reagents 2 by undergoing ring opening in the presence of a Lewis acid. Addition of 2 to tosylimines gives vic-amino alcohols with high diastereoselectivity, presumably due to a fixed conformation resulting from coordination of the metal atom. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3293 / 3296

页数：4

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