Enantioselective nitromethane addition to brominated and fluorinated benzaldehydes (Henry reaction) catalyzed by chiral bisoxazoline–copper(II) complexes

Abstract

The successful enantioselective Henry reaction of nitromethane to brominated and fluorinated benzaldehydes was achieved using a chiral bisoxazoline (unbridged)–Cu(II) complex as a catalyst. Nitroalcohols were obtained in excellent yields (up to 99%) and with enantioselectivities up to >99%. Theoretical calculations support the idea that the unbridged bisoxazoline–Cu(II) complex behaves similarly to the privileged bisoxazolines as catalysts in the Henry reaction.