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Asymmetric β-arylation of cyclopropanols enabled by photoredox and nickel dual catalysis

Jianhua Wang, Xiaoxun Li

2022Chemical Science20 citationsDOIOpen Access PDF

Abstract

The enantioselective functionalization and transformation of readily available cyclopropyl compounds are synthetically appealing yet challenging topics in organic synthesis. Here we report an asymmetric β-arylation of cyclopropanols with aryl bromides enabled by photoredox and nickel dual catalysis. This dual catalytic transformation features a broad substrate scope and good functional group tolerance at room temperature, providing facile access to a wide array of enantioenriched β-aryl ketones bearing a primary alcohol moiety in good yields with satisfactory enantioselectivities (39 examples, up to 83% yield and 90% ee). The synthetic value of this protocol was illustrated by the concise asymmetric construction of natural product calyxolane B analogues.

Topics & Concepts

Dual (grammatical number)NickelChemistryCatalysisPhotoredox catalysisCombinatorial chemistryPhotochemistryOrganic chemistryPhotocatalysisLiteratureArtRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Asymmetric β-arylation of cyclopropanols enabled by photoredox and nickel dual catalysis | Litcius