Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions

Qinglin Zhang, Jiayin Zhang, Wangjie Zhu, Ruimin Lu and Chang Guo ()
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Qinglin Zhang: University of Science and Technology of China
Jiayin Zhang: University of Science and Technology of China
Wangjie Zhu: University of Science and Technology of China
Ruimin Lu: University of Science and Technology of China
Chang Guo: University of Science and Technology of China

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Precision control of stereochemistry in radical reactions remains a formidable challenge due to the prevalence of incidental racemic background reactions resulting from undirected substrate oxidation in the absence of chiral induction. In this study, we devised an thoughtful approach—electricity-driven asymmetric Lewis acid catalysis—to circumvent this impediment. This methodology facilitates both asymmetric dienylation and allylation reactions, resulting in the formation of all-carbon quaternary stereocenters and demonstrating significant potential in the modular synthesis of functional and chiral benzoxazole-oxazoline (Boox) ligands. Notably, the involvement of chiral Lewis acids in both the electrochemical activation and stereoselectivity-defining radical stages offers innovative departures for designing single electron transfer-based reactions, significantly underscoring the relevance of this approach as a multifaceted and universally applicable strategy for various fields of study, including electrosynthesis, organic chemistry, and drug discovery.

Date: 2024
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DOI: 10.1038/s41467-024-48936-4

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