Enantioseparation of secondary alcohols by diastereoisomeric salt formation.
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.
Kiss
Violetta
V
Department of Organic Chemical Technology, Budapest University of Technology and Economics, Budapest, PO Box 91, II-1251 Hungary. vikiss@mail.bme.hu
Egri
Gabriella
G
Bálint
József
J
Fogassy
Elemér
E
D000438:Alcohols / Q000032:analysis / Q000737:chemistry*; D002849:Chromatography, Gas / Q000379:methods; D008298:Maleates / Q000737:chemistry; D008956:Models, Chemical; D012492:Salts / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D008298:Maleates; D012492:Salts; C030272:maleic acid