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Direct anti-Selective Catalytic Asymmetric Mannich-Type Reactions of α-Ketoanilides for the Synthesis of γ-Amino Amides and Azetidine-2-amides

Authors


  • We thank Z. Chen and H. Mihara at the University of Tokyo for helpful advice on this project, and T. Nitabaru and H. Morimoto for X-ray crystallography. This research was supported by Grants-in-Aid for Scientific Research (S), Scientific Research on Priority Areas (No. 20037010, Chemistry of Concerto Catalysis) (S.M.), and Young Scientists (A) (S.M.) from the JSPS and MEXT.

Abstract

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

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