On the Enantioselective Phosphoric-Acid-Catalyzed Hantzsch Synthesis of Polyhydroquinolines
Ophélie Quinonero, Clément Lemaitre, Marion Jean, Nicolas Vanthuyne, Christian Roussel, Damien Bonne, Thierry Constantieux, Cyril Bressy, Xavier Bugaut, Jean Rodriguez
Abstract
A reinvestigation of a chiral phosphoric-acid-catalyzed four-component Hantzsch enantioselective synthesis of polyhydroquinolines reported in 2009 is presented. In our hands, when the reaction was performed with fidelity to the original report using a chiral enantiopure phosphoric acid catalyst, no enantioselectivity was observed. Unlike in the original report, enantioselectivity results are backed by baseline separation of the enantiomers by HPLC analyses on chiral stationary phase with UV and chiroptical detection.
Topics & Concepts
Enantiopure drugEnantioselective synthesisPhosphoric acidChemistryEnantiomerCatalysisChiral resolutionOptically activeChiral stationary phaseCombinatorial chemistryOrganic chemistryStereoisomerismChiral column chromatographyMolecular spectroscopy and chiralityAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and Catalysis