title: Michael addition initiated carbocyclization sequences with nitroolefins for the stereoselective synthesis of functionalized heterocyclic and carbocyclic systems.
abstract: The synthesis of various heterocycles and carbocycles (tetrahydrofurans, pyrrolidines, cyclopentanes) has been achieved by using new and efficient ionic addition/cyclization sequences. Nitroolefins play an important role in the Michael addition induced ring-closing reactions (MIRC) reported in the present article, with various substituted alcohols, amines, Grignard reactants, or malonate derivatives acting as the nucleophile partner. The optimized cascade reactions were high yielding in most cases and highly stereoselective, creating up to three stereogenic centers starting from achiral substrates.
authors.affiliation: Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille iSm2 CNRS UMR 6263, Centre Saint Jérôme service 531-13397 Marseille Cedex 20, France.
authors.forename: Estelle
authors.initials: E
authors.lastname: Dumez
authors.forename: Anne-Catherine
authors.initials: AC
authors.lastname: Durand
authors.forename: Martial
authors.initials: M
authors.lastname: Guillaume
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Roger
authors.forename: Robert
authors.initials: R
authors.lastname: Faure
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Pons
authors.forename: Gaëtan
authors.initials: G
authors.lastname: Herbette
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Dulcère
authors.forename: Damien
authors.initials: D
authors.lastname: Bonne
authors.forename: Jean
authors.initials: J
authors.lastname: Rodriguez
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003517:Cyclopentanes; D003521:Cyclopropanes; D005663:Furans; D006571:Heterocyclic Compounds