S. Gobolos et al., Reductive transamination of methoxyacetone with benzylamine over Pd/SiO2 catalyst modified with anchored chiral compounds, CATAL LETT, 61(3-4), 1999, pp. 143-149
Methoxyacetone was transaminated with benzylamine to methoxyisopropylamine
over a Pd/SiO2 catalyst modified with L-alaninol or L-phenylalaninol covale
ntly anchored to the surface of the support via an organo-silicon spacer gr
oup. In the first step of transamination a Schiff base was formed from the
ketone and benzylamine, and then it was hydrogenated in the second step on
the chirally modified Pd/SiO2 catalysts to an asymmetric secondary amine (N
-benzyl-methoxyisopropylamine). In the third step the hydrogenolysis of the
asymmetric secondary amine resulting in methoxyisopropylamine and toluene
was carried out over a 10 wt% Pd/C catalyst. The highest enantiomeric exces
s of (S)-methoxyisopropylamine was observed in cyclohexane (ee = -20-21%) u
sing anchored L-alaninol as a chiral modifier.