Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected β-amino acids

A proof of concept for the asymmetric organocatalytic aza-Michael addition reaction of nitrogen nucleophiles with simple and readily available alkyl enoates as acceptor molecules in the presence of a chiral phase-transfer catalyst has been demonstrated. The desired enantiomerically enriched beta-amino acid derivatives were obtained in up to 86% yield and with enantioselectivities of up to 37% ee. (C) 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:202209, 2012; View this article online at . DOI 10.1002/hc.21004