SmI2-promoted imino-Reformatsky reaction for facile synthesis of enantioenriched β-amino acid esters

Abstract

A facile and efficient method for the stereoselective synthesis of β-amino acid esters via SmI2-promoted imino-Reformatsky reaction is described. Asymmetric addition of tert-butyl bromoacetate to N-tert-butanesulfinyl aldimines afforded β-amino acid esters in moderate to high yields with excellent diastereoselectivities. The synthetic utilities of the tert-butyl β-amino acid esters were expanded by the preparation of β-lactams and 3-aminoindan-1-ones derivatives.