The propargylic route as a short and versatile entry to optically active monofluorinated compounds.
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.
Prakesch
Michaël
M
ENSCR, Laboratoire de Synthèses et Activations de Biomolécules, CNRS UMR 6052, Avenue du Général Leclerc, 35700 Rennes, France.
Grée
Danielle
D
Grée
René
R
D000480:Alkynes / Q000737:chemistry*; D001685:Biological Factors / Q000138:chemical synthesis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D013237:Stereoisomerism
D000480:Alkynes; D001685:Biological Factors; D006845:Hydrocarbons, Fluorinated