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- Title
Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols.
- Authors
Yang, Can; Zhou, Xiaoyu; Shen, Lixing; Ke, Zhuofeng; Jiang, Huanfeng; Zeng, Wei
- 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. Molecular rearrangements are ubiquitous in modern synthetic chemistry, providing a powerful strategy to arrive at complex structures in an atom- and step-economic process. Here, the authors disclose a Mn(I)- catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols via C-C σ-bond activation to site-selectively reorganize carbon skeletons.
- Subjects
SIGMATROPIC rearrangements; ALLYL alcohol; REARRANGEMENTS (Chemistry); ALCOHOL; CARBONYL compounds; KETONES; SKELETON
- Publication
Nature Communications, 2023, Vol 14, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-023-37299-x