Enantioselective radical reactions: Stereoselective aldol synthesis from cyclic ketones

被引：16
|
作者：
Sibi, Mukund P. [1 ]
Nad, Sukanya [1 ]
机构：
[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 48期
关键词：
chiral Lewis acids; enantioselectivity; ketone aldols; radical reactions; rotamer geometry;
D O I：
10.1002/anie.200702976
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Radicalized aldols: Enones with a fixed s-cis geometry can undergo enantioselective radical reactions. The synthesis of aldol products derived from cyclic ketones in excellent yields and enantioselectivity demonstrates that s-cis-enones are excellent substrates for radical reactions. A tentative model to explain the stereochemical outcome of the reaction consists of nucleophilic radical addition to the si face (see picture). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：9231 / 9234
页数：4
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