Dual Nickel/Photoredox-Catalyzed Regio- and Enantioselective Alkenylation of Epoxides.

Authors

Hongyan Lan, Shengzhou Jin, Zhao-Dong Xu, Guigen Li, Dingyi Wang

Published in

Advanced science (Weinheim, Baden-Wurttemberg, Germany). Pages e77326. Aug 29, 2026. Epub Aug 29, 2026.

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.

PMID:
42666075
Bibliographic data and abstract were imported from PubMed on 29 Aug 2026.

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