title: The propargylic route as a short and versatile entry to optically active monofluorinated compounds.
abstract: Using selected models and appropriate NMR techniques, it has been demonstrated that dehydroxyfluorination in the propargylic position can be highly regio- and stereoselective. The corresponding propargylic fluorides are very useful intermediates for short preparations of stereodefined unsaturated or polyunsaturated compounds with a single fluorine atom in allylic or propargylic position. This strategy offers good means for the synthesis of chiral, nonracemic monofluorinated analogues of natural products.
authors.affiliation: ENSCR, Laboratoire de Synthèses et Activations de Biomolécules, CNRS UMR 6052, Avenue du Général Leclerc, 35700 Rennes, France.
authors.forename: Michaël
authors.initials: M
authors.lastname: Prakesch
authors.forename: Danielle
authors.initials: D
authors.lastname: Grée
authors.forename: René
authors.initials: R
authors.lastname: Grée
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001685:Biological Factors / Q000138:chemical synthesis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001685:Biological Factors; D006845:Hydrocarbons, Fluorinated