Palladium-catalyzed diastereo- and enantioselective desymmetric hydrophosphination of cyclopropenes

Cyclopropanes are unique three-member rings whose unusual bonding and inherent ring strain make them valuable building blocks in modern organic synthesis. In this work, a Pd-catalyzed diastereo- and enantioselective desymmetric hydrophosphination of 3,3-disubstituted cyclopropenes is described. It allows efficient, direct, and atom-economic access to potentially valuable chiral cyclopropane rings bearing two vicinal carbon stereocenters in high yields with excellent diastereo- and enantioselectivities (up to >98:2 d.r. [diastereomeric excess] and 97% ee [enantiometric excess]). Further transformations of these chiral phosphorus-containing three-member rings provide a range of potential applications.