title: Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter.
abstract: An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylamine was found to be the most effective catalyst when using trans-β-methyl-β-nitrostyrenes affording the heterocyclic products in good yields and moderate stereoselectivities.
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Via Giovanni Paolo II, 84084, Fisciano, Italy.
authors.forename: Sara
authors.initials: S
authors.lastname: Meninno
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Via Giovanni Paolo II, 84084, Fisciano, Italy.
authors.forename: Chiara
authors.initials: C
authors.lastname: Volpe
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Via Giovanni Paolo II, 84084, Fisciano, Italy.
authors.forename: Giorgio
authors.initials: G
authors.lastname: Della Sala
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Via Giovanni Paolo II, 84084, Fisciano, Italy.
authors.forename: Amedeo
authors.initials: A
authors.lastname: Capobianco
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Via Giovanni Paolo II, 84084, Fisciano, Italy.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Lattanzi
keywords: amine thioureas; aymmetric synthesis; cascade reaction; organocatalysis; tetrahydrothiophenes