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Stereospecific Reaction of Donor-Acceptor Cyclopropanes with Thioketones: A Novel Access to Highly Substituted Tetrahydrothiophenes

Augustin, André U ORCID; Sensse, Maximilian; Jones, Peter G; Werz, Daniel B ORCID

Lewis-acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield when using AlCl3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur-bridged [n.2.1] bicyclic ring systems. Conversion of selenoketones, the heavier analogues, under similar conditions resulted in the formation of various tetrahydroselenophenes.

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Augustin, A.U., Sensse, M., Jones, P.G., Werz, D.B., 2017. Stereospecific Reactions of Donor-Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes. https://doi.org/10.24355/dbbs.084-202002261253-0
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License Holder: This is the peer reviewed version of the following article: Stereospecific Reaction of Donor-Acceptor Cyclopropanes with Thioketones: A Novel Access to Highly Substituted Tetrahydrothiophenes, which has been published in final form at https://doi.org/10.1002/anie.201708346. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.

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