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Copper‐Catalyzed Amination of Ketene Silyl Acetals with Hydroxylamines: Electrophilic Amination Approach to α‐Amino Acids
Author(s) -
Matsuda Naoki,
Hirano Koji,
Satoh Tetsuya,
Miura Masahiro
Publication year - 2012
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.201206755
Subject(s) - amination , electrophilic amination , umpolung , ketene , chemistry , electrophile , catalysis , silylation , organic chemistry , amino acid , pentane , combinatorial chemistry , medicinal chemistry , nucleophile , biochemistry
Role reversal : The title reaction has been developed to deliver α‐amino acids under very mild reaction conditions (see scheme; dpppen=1,5‐bis(diphenylphosphino)pentane). The catalysis provides a new CN bond‐forming approach for the synthesis of α‐amino acids by using an umpolung, electrophilic amination strategy.