Organocatalytic Enantioselective Synthesis of α-Fluoro-β-amino Acid Derivatives.

Abstract

Asymmetric cyclocondensation of N-sulfonylimines with fluoroacetic acid promoted by isothiourea catalyst HBTM-2 generates 3-fluoro-β-lactams with high enantio- and diastereoselectivity. These reactive compounds are opened with alcohols or amines to produce the corresponding α-fluoro-β-amino acid derivatives in moderate yields.