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Stereoselective Amination of Chiral Enolates: Synthesis of enantiomerically pure α,β-Diamino Acids, Chiral Key Compounds in the Synthesis of Conformationally Constrained Peptido- and Non-peptidomimetics.
This work describes an efficient synthesis of enantiomerically pure (R)-2-aminomethylalanine, (R)-2-aminomethylnorvaline, (R)-2-aminomethylvaline, (R)-2-aminomethylleucine and (R)-2-aminomethylphenylalanine by electrophilic amination of chiral 2-cyanoesters with O-(diphenylphosphinyl)hydroxylamine followed by appropriate reduction and hydrolysis.