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Copper‐Catalyzed Enantioselective Formation of C−CF 3 Centers from β‐CF 3 ‐Substituted Acrylates and Acrylonitriles

Abstract : The catalytic asymmetric synthesis of β‐trifluoromethylated esters or nitriles is reported. The use of an in situ formed chiral Cu−H complex allowed the enantioselective reduction of β‐trifluoromethylated acrylates or acrylonitriles. The reaction proceeds smoothly affording the corresponding enantioenriched products in good to excellent yields and outstanding enantioselectivities (up to 98 % ee). The mechanism of the reaction was studied, and a plausible reaction pathway was suggested accordingly. Finally, the versatility of the products was highlighted through functional group manipulations.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02419513
Contributor : Madeleine Roux-Merlin <>
Submitted on : Thursday, December 19, 2019 - 3:08:26 PM
Last modification on : Thursday, July 2, 2020 - 3:29:27 AM

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Pauline Poutrel, Maria V. Ivanova, Xavier Pannecoucke, Philippe Jubault, Thomas Poisson. Copper‐Catalyzed Enantioselective Formation of C−CF 3 Centers from β‐CF 3 ‐Substituted Acrylates and Acrylonitriles. Chemistry - A European Journal, Wiley-VCH Verlag, 2019, 25 (67), pp.15262-15266. ⟨10.1002/chem.201904192⟩. ⟨hal-02419513⟩

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