On the Relation between Elution Order and Absolute Stereochemistry of Alkylarylcarbinols from a Pirkle Column

Article abstract of DOI:10.1021/jo00152a010

A study of the relation between the absolute stereochemistry of a series of alkylarylcarbinols and two groups of benzocycloalkenols with their elution order from an HPLC column containing a chiral stationary phase has shown that the enantiomer more strongly retained by the column in each group of compounds has the same absolute stereochemistry except for benzoin and its p-methyl derivative.The enantiomer more strongly retained in the acyclic series does not have the same absolute stereochemistry as that retained in the two cyclic series examined.Better separations were observe d in the acyclic series for the acetate esters than the free alcohols, while the reverse situation occurred for the benzocycloalkenols.In each series of compounds the enantiomer of the alcohols and corresponding acetates more strongly retained on the column differs in absolute stereochemistry.These results are not in accord with the current model for "chiral recognition" on the chiral phase employed.The reliability of using elution order to assign the absolute stereochemistry of previously unassigned compounds is compared with other methods currently in use.