Michael addition of ketone enolates to α,β-unsaturated esters or amides in a one-pot procedure:: Highly efficient effect of lithium salt generated in situ on organotin enolate

被引：5

作者：

Yasuda, M

Shigeyoshi, Y

Shibata, I

Baba, A

机构：

[1] Osaka Univ, Dept Mol Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Handai Frontier Res Ctr, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

SYNTHESIS-STUTTGART | 2005年 / 02期

关键词：

tin enolates; ligand; Michael addition; unsaturated ester; high coordination;

D O I：

10.1055/s-2004-834933

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition of a metal ketone enolate to an alpha, beta-unsaturated ester is thermodynamically disfavored, and thus, isolated metal enolates with an equimolar amount of Lewis acids or additives are usually required. This work describes the methodology of one-pot Michael addition from the parent ketones and unsaturated esters to the products directly. The treatment of a parent ketone with sec-butyllithium and Bu3SnBr gives a highly coordinated tin enolate that is complexed with LiBr generated in situ. The species is reactive and affords the Michael adducts, delta-keto esters and amides, in the reaction with alpha,beta-unsaturated esters and amides, respectively.

引用

页码：233 / 239

页数：7