title: Asymmetric synthesis of cyclopropanes with a monofluorinated quaternary stereocenter.
abstract: New chiral fluorinated reagents (N-(dibromofluoroacetyl)oxazolidinones) were easily synthesized and used in an asymmetric cyclopropanation process. The Michael initiated ring closure reaction provided chiral cyclopropanes bearing a fluorinated quaternary stereocenter. Various electron-deficient alkenes can be used to efficiently obtain chiral polysubtituted fluorinated cyclopropanes in good yields. Moderate to very good cis/trans ratios were obtained with a high level of diastereoselectivity for each isomer.
authors.affiliation: INSA de Rouen, UMR 6014 & FR 3038, C.O.B.R.A. Université de Rouen, 1 rue Tesnière, 76131 Mont-Saint-Aignan Cedex, France.
authors.forename: Pavel
authors.initials: P
authors.lastname: Ivashkin
authors.forename: Samuel
authors.initials: S
authors.lastname: Couve-Bonnaire
authors.forename: Philippe
authors.initials: P
authors.lastname: Jubault
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
mesh_terms: D003521:Cyclopropanes / Q000138:chemical synthesis*; D005461:Fluorine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D023303:Oxazolidinones; D005461:Fluorine