Kinugasa Reaction Applied to the Synthesis of α-Amino-β-lactams

Abstract

The authors recognized the potential of diastereocontrol of the Kinusaga reaction to prepare chiral β-lactams if the alkyne bore a chiral auxiliary. Although many enantioselective synthetic entries to β-lactams have been reported in recent years, very few allow installing an α-amino group on the lactam. The diastereoselectivity obtained is excellent. Access to epimeric amine functionalities was demonstrated by reductive cleavage of the oxazoborolidinone moiety.