Copper‐Catalyzed Enantioselective Formation of C−CF 3 Centers from β‐CF 3 ‐Substituted Acrylates and Acrylonitriles - Normandie Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2019

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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hal-02419513 , version 1 (19-12-2019)

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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, 2019, 25 (67), pp.15262-15266. ⟨10.1002/chem.201904192⟩. ⟨hal-02419513⟩
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