A Disulfonimide Catalyst for Highly Enantioselective Mukaiyama–Mannich Reaction

Abstract

A new BINOL-derived chiral disulfonimide has been developed by introducing 4-methyl-3,5-dinitrophenyl substituents at its 3- and 3'-positions. This chiral disulfonimide catalyst displays high catalytic efficacy toward the asymmetric Mukaiyama-Mannich reaction of imines with ketene silyl acetals leading to β-amino acid esters in good yields (up to 99%) with high diastereoselectivities (syn/anti up to 97:3) and enantioselectivities (up to 98% ee). The long-standing problem of the chiral phosphoric acid-catalyzed asymmetric Mukaiyama-Mannich reaction that requires a 2-hydroxyphenyl moiety was solved by this disulfonimide catalyst.