Synthesis of β-iodo-α-(hydroxyalkyl)acrylates:: a convenient and stereoselective reaction

被引：30

作者：

Wei, HX ^{[1
]}

Gao, JJ ^{[1
]}

Li, GG ^{[1
]}

Paré, PW ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 32期

关键词：

Baylis Hillman adducts; diethyl aluminium iodide; methyl propynoate; beta-iodo-alpha-(hydroxyalkyl)acrylates;

D O I：

10.1016/S0040-4039(02)01106-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot, three-component coupling reaction for the synthesis of beta-iodo-alpha-(hydroxyalkyl)acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active beta-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford beta-iodo Baylis-Hillman adducts in excellent yields with high Z-selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5677 / 5680

页数：4

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