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.