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

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

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 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 analogs, under similar conditions resulted in the formation of various tetrahydroselenophenes.

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Augustin, André / Sensse, Maximilian / Jones, Peter / et al: Stereospecific Reaction of Donor-Acceptor Cyclopropanes with Thioketones. A Novel Access to Highly Substituted Tetrahydrothiophenes. 2017.

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