A number of optically active cyclohexanol and cyclohexane-1,2-diol derivatives, chiral auxiliaries and substitutes for (-1and (+)-8-phenylmenthol, have been prepared by enzymatic hydrolysis of their racemic acetates and chloroacetates in the presence of a highly selective ester hydrolase from Pseudomonas sp. (SAM-11).Enantiomerically pure compounds with cyclohexanol substructures like (-)and (+)-menthol [( -)/( +)-( l)] or (-)& phenylmenthol (-)-(2) are among the most widely used, classical chiral reagents in organic chemistry, both for analytical and synthetic applications.' Although (-)-( 2) and (+)-(2) are among the most powerful auxiliaries in asymmetric synthesis,2 synthetic routes starting from (+)-pulegone3 or (-)-pulegone ,4 respectively, are less than satisfactory, often impractical on a synthetic scale. This is also reflected in the high price of these reagents, and so more readily accessible substitutes for (-)and (+)-(2) are highly desirable. Closely related structures are phenyl-and benzyl-cyclohexanols ( R ,S)and (S,R)-( 3),(4), it was shown recently that (R,S)-( 3) is as powerful as (-)-(2) for efficient absolute stereocontrol.5 Also structurally similiar to (-)-(2) are the corresponding
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