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Impact of the Difluoromethylene Group in the Organocatalyzed Acylative Kinetic Resolution of α,α‐Difluorohydrins

Abstract : 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 a,a-difluorohydrins using a commercially available chiral isothiourea is reported through a kinetic resolution (KR) process. It reveals that the difluoromethylene moiety (C(sp 3)F 2) can serve as a directing group through electrostatic fluorine-cation interactions, 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 2,2difluoro-1,3-diols, we also demonstrated that aromatic and fluorinated groups were mutually compatible to provide the expected enantioenriched adducts with > 99:1 er.
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https://hal.archives-ouvertes.fr/hal-03420063
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Submitted on : Monday, November 8, 2021 - 11:08:08 PM
Last modification on : Thursday, August 4, 2022 - 5:14:33 PM
Long-term archiving on: : Wednesday, February 9, 2022 - 7:54:35 PM

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Titouan Desrues, Jérémy Merad, Daniela Andrei, Jean-Marc Pons, Jean-Luc Parrain, et al.. Impact of the Difluoromethylene Group in the Organocatalyzed Acylative Kinetic Resolution of α,α‐Difluorohydrins. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2021, 60 (47), pp.24924-24929. ⟨10.1002/anie.202107041⟩. ⟨hal-03420063⟩

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