Regioselective ring opening of enantiomerically enriched epoxides via catalysis with chiral (salen)Cr(III) complexes

Abstract

Chiral (salen)chromium(III)N3 complexes are demonstrated to be catalysts for the regioselective ring opening a variety of enantiomerically enriched epoxides. Selective nucleophilic attack at either epoxide carbon atom can be achieved by selection of the appropriate enantiomer of catalyst. A highly selective synthesis of norpseudoephedrine is described using this strategy.