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(sp3)−C(sp2) 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.