Synthesizing Chiral Vicinal Bisphosphine Derivatives through Hydrophosphinylation and Asymmetric Protonation of Secondary Phosphine Sulfides with Vinylphosphine Oxides

Abstract

Herein, we report bifunctional iminophosphorane-catalyzed hydrophosphinylation and asymmetric protonation of secondary phosphine sulfides with vinylphosphine oxides. This reaction efficiently afforded chiral vicinal bisphosphine derivatives in high yields with excellent enantioselectivities (up to 99% yield and 95% ee). Furthermore, the produced chiral vicinal bisphosphine derivatives could be readily transformed into vicinal bisphosphines and vicinal bisphosphine monosulfides. This study presents the first methodology for using secondary phosphine sulfides as pronucleophiles in asymmetric protonation reactions.