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

ORCID
0000-0002-6425-2843
Affiliation
Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Augustin, André U;
Affiliation
Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Sensse, Maximilian;
Affiliation
Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Jones, Peter G;
ORCID
0000-0002-3973-2212
Affiliation
Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Werz, Daniel B

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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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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