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Novel chiral N-carbamate-protected γ-amino-β-ketones 3a–c and the known N-carbamate-protected nitroketone 3d were prepared from the corresponding 1-(N-protected α-aminoacyl)benzotriazoles 1 by reaction with nucleophiles 2a–d in the presence of bases under mild conditions. Similarly achiral and chiral N-protected γ-amino-β-ketoesters 3e–l were prepared by reaction with acetoacetates in the presence of sodium hydride.

Synthesis of achiral and chiral N-protected γ-amino-β-ketones and β-ketoesters