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Synlett 1992; 1992(10): 847-848
DOI: 10.1055/s-1992-21515
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Aza-Cope Rearrangement. Asymmetric Syntheses of α-Amino Acids: (R)-Homoserine Lactone and (R,R)-4-(1-Hydroxy-1-methylethyl)proline

Claude Agami* , François Couty, Michel Poursoulis
  • *Université Pierre et Marie Curie, Laboratoire de Chimie Organique, URA 408, Tour 45, 4, place Jussieu, F-75005 Paris, France
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Publication Date:
08 March 2002 (online)

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An ene-iminium intermediate resulting from the condensation of a chiral N-homoallyl amino alcohol and glyoxal (water or formic acid solution) undergoes a cationic aza-Cope rearrangement leading to a new ene-iminium compound whose evolution depends on the medium. These diastereoselective transformations lead ultimately to enantiomerically pure α-amino acids.

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