Asymmetric synthesis of anti-α-substituted β-amino ketones from sulfinimines

Abstract

Previously unknown, enantiopure, β-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-α-substituted β-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-α-substituted isomers which did. The anti-α-substituted β-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-α-substituted β-amino esters because α-alkylation of N-sulfinyl β-amino Weinreb amide enolates resulted in poor diastereoselectivities.