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  • Catalytic asymmetric synthesis of α-(trifluoromethyl)benzylamine via cinchonidine derived base-catalyzed biomimetic 1,3-proton shift reaction
  • Add time:08/11/2019         Source:sciencedirect.com

    Here we describe catalytic asymmetric synthesis of α-(trifluoromethyl)benzylamine (1) via biomimetic transamination using chiral base. Imine 4 was isomerized to Schiff base 5 using 50 mol.% of cinchonidine derivatives as a catalyst in chloroform, methanol or acetonitrile. In the case of cinchonidine 6 as a catalyst, the reaction conducted in chloroform allowed for 79% conversion of the starting imine 4 in 52 days. The product imine 5 was obtained of (R) absolute configuration in 35% ee as individual compound without any byproducts. The catalyst 6 can be recovered (>95%) by adding n-hexane to the reaction mixture followed by a simple filtration.

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    Prev:Synthesis of trifluoromethyl-imines by solid acid/superacid catalyzed microwave assisted approach
    Next: Chirality-dependent sublimation of α)

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