Enantioselective palladium-catalyzed addition of malonates to 3,3-difluoropropenes

Monofluoroalkenes bearing a malonate unit at the β position can be synthesized by the enantioselective addition of diesters to 3,3-difluoropropenes. The difference in reactivity regarding the geometry and the substituents of the alkene of the 3,3-difluoropropenes, as well as the alkyl groups of the malonates, was studied and limitations were identified. The reaction was also performed with different 3,3-difluoropropenes. Further synthetic transformations of a newly functionalized monofluoroalkene were also accomplished.