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Yingjie Xu, Gang Lu, Shigeki Matsunaga and Masakatsu Shibasaki Direct anti-Selective Catalytic Asymmetric Mannich-Type Reactions of α-Ketoanilides for the Synthesis of γ-Amino Amides and Azetidine-2-amides Angewandte Chemie International Edition 48

Article first published online: 30 MAR 2009 | DOI: 10.1002/anie.200900670

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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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