title: Catalytic Enantioselective Synthesis of Halocyclopropanes.
abstract: A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2-haloalkenes with tert-butyl α-cyano-α-diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios. The reported methodology represents the first general catalytic enantioselective approach to halocyclopropanes.
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821, Mont Saint-Aignan Cedex, France.
authors.forename: Amandine
authors.initials: A
authors.lastname: Pons
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821, Mont Saint-Aignan Cedex, France.
authors.forename: Pavel
authors.initials: P
authors.lastname: Ivashkin
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821, Mont Saint-Aignan Cedex, France.
authors.forename: Thomas
authors.initials: T
authors.lastname: Poisson
authors.affiliation: Centre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montréal, PO Box 6128, Station Downtown, Montréal, Québec, H3C 3J7, Canada.
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821, Mont Saint-Aignan Cedex, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821, Mont Saint-Aignan Cedex, France. philippe.jubault@insa-rouen.fr.
authors.forename: Philippe
authors.initials: P
authors.lastname: Jubault
keywords: asymmetric catalysis; chiral rhodium catalyst; cyclopropane; diazo derivatives; fluorine