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Impact of the Difluoromethylene Group (CF2) in Organocatalyzed Acylative Kinetic Resolution of α,α-Difluorohydrins.

Due to the omnipresence of chiral organofluorine compounds in pharmaceutical, agrochemical and material chemistry, the development of enantioselective methods for their preparation is highly desirable. In the present study, the enantioselective organocatalyzed acylation of  α , α -difluorohydrins using a commercially available chiral isothiourea is reported through a kinetic resolution (KR) process. It reveals that the difluoromethylene moiety (sp 3 CF 2 ) can play the role of directing group through electrostatic fluorine-cation interaction, greatly improving the enantioselectivity of the KR. In this context, a broad range of fluorinated alcohols such as valuable 4,4-difluoro-1,3-diols could be synthesized with exquisite enantiocontrol (typically > 99:1 er).  Turning to 2,2-difluoro-1,3-diols, we also demonstrated that aromatic and fluorinated groups were mutually compatible to provide the expected enantioenriched adducts with > 99:1 er.  Relying on experimental and theoretical studies, this report considerably enriches the network of potential non-covalent interactions (NCI) for enantioselective acylation by chiral isothioureas.