Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1315167 | Journal of Fluorine Chemistry | 2007 | 4 Pages |
Abstract
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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Physical Sciences and Engineering
Chemistry
Inorganic Chemistry
Authors
Vadim A. Soloshonok, Manabu Yasumoto,