Direct anti-selective catalytic asymmetric Mannich-type reactions of alpha-ketoanilides for the synthesis of gamma-amino amides and azetidine-2-amides.

Breaking with convention: A homodinuclear nickel complex derived from a biphenyldiamine-based Schiff base catalyzed an anti-selective Mannich-type reaction of alpha-ketoanilides (see scheme) to afford unique building blocks for the synthesis of azetidine-2-amides and alpha-hydroxy gamma-amino amides. This approach stands in contrast to conventional Mannich-type reactions for the synthesis of beta-amino carbonyl compounds. o-Ns = o-nitrobenzenesulfonyl.