Absolute configurations of the arene oxide, trans-dihydrodiol and cis-dihydrodiol products resulting from metabolism of quinoline at the 5,6-bond

Article abstract of DOI:10.1016/0040-4039(91)80663-Q

Trans-6-bromo-5-hydroxy-5,6,7,8-tetrahydroquinoline enantiomers have been resolved via their dibenzoyltartrate salt diastereoisomers. X-ray crystallographic analysis of the (+)-dibenzoyltartrate salt obtained from reaction of (+)-dibenzoyltartaric acid and (-)-trans-6-bromo-5-hydroxy-5,6,7,8-tetrahydro-quinoline, when allied to a stereochemical correlation sequence linking the arene oxide, trans-dihydrodiol and cis-dihydrodiol enantiomers, provides an unequivocal asignment of absolute configuration for these quinoline metabolites.