Transition metal-free [2,3]-sigmatropic rearrangement in the reaction of sulfur ylides with allenoates

An unprecedented transition metal free [2,3]-sigmatropic rearrangement involving stabilized sulfur ylides and allenoates has been thoroughly established. The scope and utility of this reaction have been extensively studied resulting in C-C bond formation under mild conditions with greater than 20 ex...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-08, Vol.21 (3), p.696-612
Main Authors: García-Castro, Miguel, Moya-Utrera, Federico, Sarabia, Francisco
Format: Article
Language:English
Subjects:
Bonding
Covalent bonds
Isomers
Reagents
Room temperature
Sulfur
Transition metals
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Summary:An unprecedented transition metal free [2,3]-sigmatropic rearrangement involving stabilized sulfur ylides and allenoates has been thoroughly established. The scope and utility of this reaction have been extensively studied resulting in C-C bond formation under mild conditions with greater than 20 examples reported. A highlight of the work is the simple and fully operational process that does not involve the use of carbenes or the associated hazardous and sensitive reagents. The reaction can be performed at room temperature and using an open flask. Interestingly, the new C-C bond formation reaction is gram scalable, and the obtained isomers are readily separable, affording interesting building blocks that can be used in the preparation of complex molecules. A simple and fully operational process of [2,3]-sigmatropic rearrangement that does not involve the use of carbenes or the associated hazardous and sensitive reagents in an open flask reaction at room temperature.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00657c