Abstract
A new chiral modifier pantoyl-naphthylethylamine (PNEA) was synthesized by reductive alkylation of 1-(1-naphthyl)ethylamine with ketopantolactone. Platinum-on-alumina modified by PNEA afforded 93% ee and 100% chemoselectivity in the hydrogenation of the activated carbonyl group of 1,1,1-trifluoro-2,4-pentanedione. Reductive heat treatment and ultrasonication of the catalyst, and the use of chlorinated solvents under mild conditions (10 bar, 10 °C) enhanced the enantioselectivity. This is the first case in heterogeneous catalysis that a synthetic modifier gives more than 90% ee, better than the commonly used modifier of natural origin (cinchonidine or O-methyl-cinchonidine).
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Diezi, S., Hess, M., Orglmeister, E. et al. An efficient synthetic chiral modifier for platinum. Catal Lett 102, 121–125 (2005). https://doi.org/10.1007/s10562-005-5842-x
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DOI: https://doi.org/10.1007/s10562-005-5842-x