Microbially Mediated Enantioselective Ester Hydrolyses Utilizing Rhizopus nigricans. A New Method of Assigning the Absolute Stereochemistry of Acyclic 1-Arylalkanols

Article abstract of DOI:10.1021/jo00166a016

The fungus Rhizopus nigricans has been used to effect the enantioselective hydrolysis of 22 acetates of acyclic 1-arylalkanols.The absolute stereochemistry of all the chiral alcohols formed can be accounted for by a rule which is based on the relative sizes of substituents on the carbinol carbon.The relative sizes of substituents deduced from these hydrolyses have been compared with those assigned from Horeau's method for the same compounds and found to be identical; i.e., a phenyl group or heterocyclic ring is always larger than an alkyl group.The use of R. nigricans to prepare chiral alcohols and use of the rule to predict their configuration constitute a new method of assigning the absolute stereochemistry of secondary alcohols.With minor modifications this method can also be used to prepare gram quantities of chiral alcohols of both configurations.