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  • Title: Diastereoselective Synthesis of Biheterocyclic Tetrahydrothiophene Derivatives via Base-Catalyzed Cascade Michael-Aldol [3 + 2] Annulation of 1,4-Dithiane-2,5-diol with Maleimides.
    Author: Zhong Y, Ma S, Li B, Jiang X, Wang R.
    Journal: J Org Chem; 2015 Jul 02; 80(13):6870-4. PubMed ID: 26035462.
    Abstract:
    A highly diastereoselective intermolecular [3 + 2] annulation of 1,4-dithiane-2,5-diol to maleimides has been developed by using DABCO as a catalyst, which provides a series of highly functionalized biheterocyclic tetrahydrothiophene derivatives containing tetrahydrothiophene and pyrolidine backbones in excellent yields and diastereoselectivities (up to 98% yield and >20:1 d.r.). The cascade Michael-aldol reaction is capable of tolerating organic solvents as well as water.
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