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Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis

Augustin, André U ORCID; Busse, Marius; Jones, Peter G; Werz, Daniel B ORCID

Donor-acceptor cyclopropanes were reacted under Lewis acid catalysis with 3-thioxocyclobutanones as surrogates for disubstituted thioketenes. A broad scope of 2-substituted tetrahydrothiophenes with a semicyclic double bond was obtained under mild conditions with high functional group tolerance and in excellent yield. A sequence of a formal [3 + 2]-cycloaddition followed by the subsequent release of disubstituted ketene is postulated as the mechanism.

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Augustin, U.A., Busse, M., Jones, G.P., Werz, B.D., 2018. Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis. https://doi.org/10.24355/dbbs.084-202002261308-0
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License Holder: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.7b03961

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