Synthesis and Stereochemical Characterization of Some Optically Active 1,2-Dinaphthylethane-1,2-diols

Article abstract of DOI:10.1021/jo00103a035

Three new diols, 1,2-di(2-naphthyl)ethane-1,2-diol, 1-(1-naphthyl)-2-(2-naphthyl)ethane-1,2-diol, and 1,2-di(1-naphthyl)ethane-1,2-diol, have been prepared in optically active form by catalytic asymmetric syn-dihydroxylation of the corresponding (E)-olefins.The complete stereochemical characterization was easily accomplished by transforming them into the corresponding isopropyiidene ketals.These derivatives can be separated by HPLC on a Chiralcel OD column allowing the determination of the ee, and at same time, their CD spectra have been analyzed, allowing a safe assignment of absolute configuration in conjunction with molecular mechanics calculations and an exciton-coupling treatment.