Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr2 as promoter via a one-pot three-component reaction

被引：23

作者：

Wei, HX ^{[1
]}

Jasoni, RL ^{[1
]}

Hu, JL ^{[1
]}

Li, GG ^{[1
]}

Paré, PW ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2004年 / 60卷 / 45期

关键词：

Baylis-Hillman adducts; magnesium bromine; alpha; beta-acetylenic ketones; (Z)-beta-bromovinyl ketone;

D O I：

10.1016/j.tet.2004.08.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first time steroselective synthesis of (Z)-beta-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with alpha,beta-acetylenic ketones to form an active beta-bromo allenolate intermediate, which in turn attacks various aldehydes to afford beta-bromo Baylis-Hillman adducts in good yields and Z-selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：10233 / 10237

页数：5

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