title: Enantioseparation of secondary alcohols by diastereoisomeric salt formation.
abstract: A general method was found for the resolution of the racemic 1-phenyl-1-propanol (1) and 1-phenyl-2-propanol (2) with various resolving agents. Monoesters of the alcohols were prepared, which were then reacted with different chiral bases. Successful optical resolutions were achieved only with the maleic acid monoesters (3 and 6). Alcohol 1 has been resolved to >99% enantiomeric excess by diastereoisomeric salt formation via its maleic acid monoester (3) using cinchonidine (9) as resolving agent. Alcohol 2 has been obtained in 98% enantiomeric excess by diastereoisomeric salt formation via its the maleic acid monoester (6) using (+)-dehydroabietylamine (11) as resolving agent.
authors.affiliation: Department of Organic Chemical Technology, Budapest University of Technology and Economics, Budapest, PO Box 91, II-1251 Hungary. vikiss@mail.bme.hu
authors.forename: Violetta
authors.initials: V
authors.lastname: Kiss
authors.forename: Gabriella
authors.initials: G
authors.lastname: Egri
authors.forename: József
authors.initials: J
authors.lastname: Bálint
authors.forename: Elemér
authors.initials: E
authors.lastname: Fogassy
mesh_terms: D000438:Alcohols / Q000032:analysis / Q000737:chemistry*; D002849:Chromatography, Gas / Q000379:methods; D008298:Maleates / Q000737:chemistry; D008956:Models, Chemical; D012492:Salts / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D008298:Maleates; D012492:Salts; C030272:maleic acid