Design, synthesis, and application of a chiral sulfinamide phosphine catalyst for the enantioselective intramolecular Rauhut-Currier reaction.

ABSTRACT

A novel class of chiral sulfinamide phosphine catalysts (Xiao-Phos) are reported, which can be easily prepared from inexpensive commercially available starting materials. The Xiao-Phos catalysts showed good performance in enantioselective intramolecular Rauhut-Currier reactions, generating α-methylene-γ-butyrolactones in high yields with up to 99% ee under mild conditions. Moreover, kinetic resolution and parallel kinetic resolution were also observed with the use of two different substituted racemic precursors.