Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2

被引：35

作者：

Wei, HX ^{[1
]}

Hu, JL ^{[1
]}

Purkiss, DW ^{[1
]}

Paré, PW ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 05期

关键词：

Baylis-Hillman adducts; magnesium iodide; alpha; beta-acetylenic ketones; (Z)-beta-iodovinyl ketone;

D O I：

10.1016/S0040-4039(02)02746-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of (Z)-beta-iodovinyl ketone has been achieved with the tandem formation of C-C and C-I bonds in a three-component reaction. This new catalysis utilises MgI2 as a Lewis acid as well as an iodine source for a Michael-type addition. alpha,beta-Acetylenic ketone is initially converted to an active beta-iodo allenolate intermediate and then can be attacked by a variety of aldehydes to afford Z-selective Baylis-Hillman adducts in excellent yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：949 / 952

页数：4

共 21 条

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