Collect. Czech. Chem. Commun. 1986, 51, 401-403

Preparation of secondary alcohols of high optical purity

Otakar Červinka, Anna Fábryová and Irina Sablukova

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Partially resolved enantiomers of optically active alcohols I-V, obtained by enantioselective reduction of the corresponding ketones with lithium aluminium hydride in the presence of (-)-quinine, were converted into crystalline 3,5-dinitrobenzoates or phenylcarbamates. The esters of the nearly optically pure enantiomers were separated by crystallization from the generally more soluble esters of the racemates. Optical purity of the hydrolytically liberated alcohols was determined by 1H NMR spectroscopy in the presence of chiral shifting agents.