Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Bronsted acids

被引：296

作者：

McDougal, NT ^{[1
]}

Schaus, SE ^{[1
]}

机构：

[1] Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 40期

关键词：

D O I：

10.1021/ja037705w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral BINOL-derived Brønsted acids catalyze the enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2-20 mol % of the chiral Brønsted acid 2e or 2f and triethylphosphine as the nucleophilic promoter. The reaction products are obtained in good yields (39-88%) and high enantioselectivities (67-96% ee). The Brønsted-acid-catalyzed reaction is the first example of a highly enantioselective asymmetric MBH reaction of cyclohexenone with aldehydes. Copyright © 2003 American Chemical Society.

引用

页码：12094 / 12095

页数：2

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