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

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.

Graphical abstractAn efficient asymmetric Michael addition of Grignard reagents to aryl substituted α,β-unsaturated carbonyl compounds (1) has been developed. The reaction exhibits high regioselectivity and diastereoselectivity (up to 99:1).Download full-size image