(4 + 3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to
André U Augustin1, J Luca Merz1, Peter G Jones1
1Technische Universität Braunschweig , Institute of Organic Chemistry and Institute of Inorganic and Analytical Chemistry , Hagenring 30 , 38106 Braunschweig , Germany.
Abstract:
A general approach is described for the formation of tetrahydrothiepines using donor-acceptor cyclopropanes. Thiochalcones, functioning as sulfur-containing four-atom building blocks, were reacted in a Lewis acid catalyzed formal (4 + 3)-cycloaddition reaction with donor-acceptor cyclopropanes as three-atom building blocks. Under mild conditions various tetrahydrothiepines were synthesized in good yields in a stereospecific reaction with high functional group tolerance.
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