Chemoselectivity and enantiocontrol in catalytic intramolecular metal carbene reactions of diazo acetates linked to reactive functional groups by naphthalene-1,8-dimethanol

Abstract

The use of chiral dirhodium(II) carboxamidate catalysts for metal carbene transformations of diazo acetates linked to a reactive functionality through naphthalene-1,8-dimethanol produces chemoselective and enantioselective reaction either at the remote functionality or by addition to the 1,2-position of the naphthalene ring; enantioselectivities up to 84% ee have been obtained for the Büchner reaction.