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.
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.
authors.affiliation: †School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, China.|‡School of Life Sciences, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Zhong
authors.affiliation: ‡School of Life Sciences, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China.
authors.forename: Shixiong
authors.initials: S
authors.lastname: Ma
authors.affiliation: †School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, China.
authors.forename: Bai
authors.initials: B
authors.lastname: Li
authors.affiliation: †School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, China.
authors.forename: Xianxing
authors.initials: X
authors.lastname: Jiang
authors.affiliation: †School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, China.|‡School of Life Sciences, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China.
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006571:Heterocyclic Compounds; D008301:Maleimides; D013457:Sulfur Compounds; D013876:Thiophenes; C060568:1,4-dithiane; C121030:tetrahydrothiophene