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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
Author(s) -
Xu Yingjie,
Lu Gang,
Matsunaga Shigeki,
Shibasaki Masakatsu
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900670
Subject(s) - azetidine , chemistry , catalysis , mannich reaction , mannich base , schiff base , stereochemistry , combinatorial chemistry , organic chemistry , medicinal chemistry
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.