Palladacycle catalyzed asymmetric P-H addition of diarylphosphines to N-enoyl phthalimides

Abstract

The first asymmetric phospha-Michael addition of diarylphosphines to N-enoyl phthalimides has been developed in the presence of a chiral palladacycle catalyst. A library of free chiral tertiary phosphine adducts were directly obtained with excellent yields and enantioselectivities. Products can be subsequently functionalized to afford β-phosphinoamides, the direct preparation of which from cinnamides has been notoriously challenging.

Keywords: Michael addition; asymmetric catalysis; hydrophosphination; imides; palladacycles; phosphines.