Asymmetric synthesis of α-monofluoromethyl- and α-difluoromethylbenzylamines through regioselective hydrogenolysis

Asymmetric synthesis of α-monofluoromethyl- and α-difluoromethylbenzylamines through regioselective hydrogenolysis is described. Hydrogenolysis of diastereomerically pure bis(α-methylbenzyl)amine derivatives having partially fluorinated methyl group at benzylic position also proceeded with a high regioselectivity as well as in the case of α-trifluoromethyl group. Moreover, opposite asymmetric induction was observed in reduction of chiral imines derived from partially fluorinated acetophenone and α-phenylethylamine.