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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

2009; Wiley; Volume: 48; Issue: 18 Linguagem: Inglês

10.1002/anie.200900670

1521-3773

Yingjie Xu, Gang Lü, Shigeki Matsunaga, Masakatsu Shibasaki,

Asymmetric Hydrogenation and Catalysis

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. magnified image