Dual Nickel/Photoredox‐Catalyzed Regio‐ and Enantioselective Alkenylation of Epoxides

Abstract

ABSTRACT β ‐Chiral phenethyl alcohols represent a privileged scaffold in bioactive molecules, chemical probes, and functional materials, serving as versatile synthons in organic synthesis. Herein, we report the first Ni/photoredox‐catalyzed stereoconvergent C(sp 3 )−C(sp 2 ) cross‐electrophile coupling of racemic epoxides with alkenyl bromides, delivering β ‐alkenyl phenylethanol with high enantioselectivity (up to 95% ee), excellent E ‐stereoselectivity, and complete regiocontrol. The enantioenriched products serve as versatile intermediates for diverse chiral synthons, enabling further applications. Mechanistic studies suggest a stereoconvergent pathway involving regioselective halide ring‐opening of epoxides, followed by enantioselective coupling of the generated β ‐hydroxy benzyl halides with alkenyl bromides.