Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols

Can Yang, Xiaoyu Zhou, Lixing Shen, Zhuofeng Ke (), Huanfeng Jiang and Wei Zeng ()
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Can Yang: South China University of Technology
Xiaoyu Zhou: Sun Yat-sen University
Lixing Shen: South China University of Technology
Zhuofeng Ke: Sun Yat-sen University
Huanfeng Jiang: South China University of Technology
Wei Zeng: South China University of Technology

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Sigmatropic rearrangement provides a versatile strategy to site-selectively reorganize carbon-skeleton with high atom- and step-economy. Herein, we disclose a Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols via C-C σ bond activation. A variety of α-aryl-allylic alcohols and α-aryl-propargyl alcohols could undergo in-situ 1,2- or 1,3- sigmatropic rearrangements to allow for converting to complex structural arylethyl- and arylvinyl- carbonyl compounds under a simple catalytic system. More importantly, this catalysis model can be further applied to assemble macrocyclic ketones through bimolecular [2n + 4] coupling-cyclization and monomolecular [n + 1] ring-extension. The presented skeleton rearrangement would be a useful tool complementary to the traditional molecular rearrangement.

Date: 2023
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DOI: 10.1038/s41467-023-37299-x

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