Enantiomerically pure α-pinene derivatives from material of 65% enantiomeric purity.: Part 1:: Di[3α-(2α-hydroxy)pinane]amine

By making use of differences in the physical properties of crystallographically different heteroenantiomeric racemic compounds and pure enantiomers, a convenient method for the preparation of enantiomerically pure 2alpha-hydroxypinan-3-one and its oxime was developed. The enantiomerically pure compounds were used in syntheses of pinane amino alcohols, which proved to be useful ligands for catalytic applications in processes such as asymmetric reduction of prochiral ketones, asymmetric alkylation of aldehydes, and Diels-Alder reactions. Optically active tert-butylphenylphosphinothioic acid was found to be a versatile chiral solvating agent for the rapid determination of enantiomeric excess of the above compounds by H-1 NMR spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.