title: A straightforward and highly diastereoselective access to functionalized monofluorinated cyclopropanes via a Michael initiated ring closure reaction.
abstract: The synthesis of highly functionalized monofluorinated cyclopropanes based on a Michael Initiated Ring Closure (MIRC) reaction has been developed. The addition of quaternary ammonium salts derived from ethyl bromofluoroacetate on a panel of electron deficient alkenes followed by cyclization gave rise to an efficient access to monofluorinated cyclopropanes with good yields and remarkable diastereoselectivity.
authors.affiliation: Normandie Université, COBRA, UMR 6014 et FR 3038; Université de Rouen; INSA Rouen; CNRS , 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France.
authors.forename: Thibault
authors.initials: T
authors.lastname: Ferrary
authors.forename: Emilie
authors.initials: E
authors.lastname: David
authors.forename: Gaëlle
authors.initials: G
authors.lastname: Milanole
authors.forename: Tatiana
authors.initials: T
authors.lastname: Besset
authors.forename: Philippe
authors.initials: P
authors.lastname: Jubault
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
mesh_terms: D000475:Alkenes / Q000737:chemistry; D064751:Ammonium Compounds / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D064751:Ammonium Compounds; D003521:Cyclopropanes; D006845:Hydrocarbons, Fluorinated