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Synlett 1991; 1991(9): 649-650
DOI: 10.1055/s-1991-20828
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Anionic Hetero[3,3] Rearrangements. N-Acylhydroxylamine-O-carbamates to α-Amino Acids: A New Method for Introduction of Amino Groups at the α-Position of Carboxylic Acids

Yasuyuki Endo* , Shoji Hizatate, Koichi Shudo
  • *Faculty of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113, Japan
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07. März 2002 (online)

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N-Acylhydroxylamine-O-carbamates rearrange under basic conditions to afford α-amino acid amide derivatives. The rearrangement, which can be rationalized in terms of [3,3] sigmatropic shifts, is applicable to α-amination of carboxylic acids.