ISSN:
1572-879X
Keywords:
enantioselective amination
;
reductive transamination
;
enantioselective hydrogenation
;
Schiff base
;
methoxyisopropylamine
;
chiral modifiers
;
methoxyacetone
;
palladium catalysts
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Methoxyacetone was transaminated with benzylamine to methoxyisopropylamine over a Pd/SiO2 catalyst modified with L‐alaninol or L‐phenylalaninol covalently anchored to the surface of the support via an organo‐silicon spacer group. 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 excess of (S)‐methoxyisopropylamine was observed in cyclohexane (ee = −20–21%) using anchored L‐alaninol as a chiral modifier.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1019081107629
