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. 2017 Nov 6;56(45):14293-14296.
doi: 10.1002/anie.201708346. Epub 2017 Oct 10.

Stereospecific Reactions of Donor-Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes

André U Augustin  1 , Maximilian Sensse  1 , Peter G Jones  2 , Daniel B Werz  1
Affiliations

Stereospecific Reactions of Donor-Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes

André U Augustin et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: bicyclic systems; cycloaddition; cyclopropanes; donor-acceptor compounds; thiocarbonyls.

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