受主-给体环丙烷与硫代酮的立体专一反应：高取代四氢噻吩的合成。
Stereospecific Reactions of Donor-Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes.
机构信息
Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
出版信息
Angew Chem Int Ed Engl. 2017 Nov 6;56(45):14293-14296. doi: 10.1002/anie.201708346. Epub 2017 Oct 10.
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 AlCl 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.
描述了 2-取代环丙烷 1,1-二羧酸酯与硫代酮的路易斯酸催化反应。在温和条件下，使用 AlCl 作为路易斯酸，可以以立体定向方式获得高度取代的具有两个相邻季碳原子的四氢噻吩，并以高产率得到。此外，还成功实施了一种分子内方法来获得硫桥接[n.2.1]双环体系。在类似条件下，硒代酮（较重的类似物）的转化导致各种四氢硒吩的形成。
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