Enantioselective Ester Hydrolyses Employing Rhizopus nigricans. A Method of Preparing and Assigning the Absolute Stereochemistry of Cyclic Alcohols

Article abstract of DOI:10.1021/jo00178a020

The mold Rhizopus nigricans has been used to hydrolyze enantioselectively the acetates of several series of benzocycloalken-3-ols and 2-substituted cycloalkanols to yield chiral alcohols.The configurations of the alcohols formed were established.The absolute stereochemistries of 25 of the 26 alcohols obtained were found to conform to a generalization based on the effective sizes of substituents on the carbinol carbon.The relative sizes of substituents required for agreement were identical with those employed in Horeu's method of establishing the absolute stereochemistry of the same compounds.The use of these microbially mediated hydrolyses to assign the absolute stereochemistry of cyclic secondary alcohols is compared to Horeau's method and to the use of empirical relations between the absolute stereochemistry of an enantiomer and the order, relative to its antipode, in which it is eluted from a chiral (Pirkle) column.