Diastereoselective Synthesis of Phosphinyl Peptides via Rh-Catalyzed 1,4-Addition in Coparticipation of a P-Chiral Moiety and Difluorphos.

ABSTRACT

The asymmetric Rh-catalyzed 1,4-addition of aryl/heteroaryl moieties to α,ß-unsaturated esters was achieved in high diastereoselectivity via the coparticipation of a P-chiral phosphinyl moiety at Cß to the prochiral center and (R)- or (S)-Difluorphos. This methodology expands the synthetic toolbox available for the preparation of structurally diverse chiral phosphinyl peptides.