Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 345, Issue 1-2, Pages 165-168Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200390004
Keywords
asymmetric heterogeneous catalysis; diastereoselective hydrogenation; hydrogenolysis; palladium; 2,2,2-trifluoro-1-phenylethyl amines
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The synthesis of chiral 2,2,2-trifluoro-1-phenylethylamines by palladium-catalyzed diaster-eoselective heterogeneous catalytic hydrogenation is described. The one-pot process involves two steps; the diastereoselective hydrogenation of chiral 2,2,2,2-trifluoro-1-phenylethyl-N-1'-phenylethylimines and the hydrogenolysis of the methylbenzyl group on the amino function. During both the hydrogenation and hydrogenolysis steps favorable stereoinduction was observed, and the products were obtained in 90-93% ee and 50-55% yield.
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