Kinetic Resolution of Racemic 3,4-Disubstituted 1,4,5,6-Tetrahydropyridine and 3,4-Disubstituted 1,4- Dihydropyridines via Rh-Catalyzed Asymmetric Hydrogenation
Wendian Li, Hailong Yang, Ruihao Li, Hui Lv, Xumu Zhang
Abstract
Kinetic resolution of racemic 3,4-disubstituted 1,4,5,6-tetrahydropyridines and 3,4-disubstituted 1,4-dihydropyridines was developed by Rh-catalyzed asymmetric hydrogenation, affording chiral 3,4-disubstituted piperidines and chiral 3,4-disubstituted 1,4,5,6-tetrahydropyridines with high selectivity factors (s = up to 1057). Remarkably, all four stereoisomers of 3,4-disubstituted piperidine can be easily prepared using our developed method. Furthermore, the synthetic utility of this methodology was demonstrated by efficient synthesis of antidepressant drug (−)-paroxetine.
Topics & Concepts
Kinetic resolutionPiperidineChemistrySelectivityCatalysisAsymmetric hydrogenationEnantioselective synthesisCombinatorial chemistryStereochemistryOrganic chemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods