Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes
Pauline Poutrel, Xavier Pannecoucke, Philippe Jubault, Thomas Poisson
Abstract
Herein we report the hydrodefluorination reaction of trifluoromethylated alkenes to access terminal monofluoroalkenes. The use of LiAlH4 allowed the stereoselective synthesis of the terminal monofluoroalkenes in good to excellent yields with good to excellent diastereoselectivities. Mechanistic studies suggested a hydroalumination reaction followed by a stereoselective fluoride elimination.
Topics & Concepts
ChemistryStereoselectivityTerminal (telecommunication)FluorideCombinatorial chemistryOrganic chemistryStereochemistryCatalysisInorganic chemistryComputer scienceTelecommunicationsFluorine in Organic ChemistryInorganic Fluorides and Related Compounds