On the Absolute Stereochemistries of (-)-Benzocyclohepten-3-ol, (-)-2,3,4,5-Tetrahydro-1-benzoxepin-5-ol, and (-)-Benzocycloocten-3-ol

Article abstract of DOI:10.1021/jo00153a018

The configurations of (-)-benzocyclohepten-3-ol (2a), (-)-2,3,4,5-tetrahydro-1-benzoxepin-5-ol (6a), and (-)-benzocycloocten-3-ol (9a), which were prepared by microbial reduction of the corresponding keto compounds by Cryptococcus macerans, were established as S by conversion to dimethyl α-acetoxy dicarboxylate esters of known configuration.The elution order of the enantiomers of each of these three carbinols and their acetates from a Pirkle chiral-phase HPLC column was not consistent with that found for the lower homologues, 1-indanol and 1-tetralol.These results indicat e great care must be exercised in the use of elution order for the determination of configurations.