Tetrahedron

Regio-and diastereoselective conjugate addition of Grignard reagents to aryl substituted α, β-unsaturated carbonyl compounds derived from Oppolzer's sultam

X Cao, F Liu, W Lu, G Chen, GA Yu, SH Liu

Index: Cao, Xiufang; Liu, Fang; Lu, Wenchang; Chen, Gang; Yu, Guang-Ao; Liu, Sheng Hua Tetrahedron, 2008 , vol. 64, # 24 p. 5629 - 5636

Full Text: HTML

Citation Number: 23

Abstract

Asymmetric conjugate addition of Grignard reagents to aryl substituted α, β-unsaturated carbonyl compounds (1) has been achieved with great regioselectivity (> 20: 1) and good to excellent diastereoselectivity (de up to 98%). The nucleophilicity and stereospecific blockade of the Grignard reagents play a key role in controlling the regioselectivities and diastereoselectivities of the conjugate addition reaction.