Determination of the Absolute Configuration of 1-Arylethane-1,2-diols by a Nonempirical Analysis of the CD Spectra of Their 4-Biphenylboronates

<UFIGR ID="ol9911461n00001">1-Arylethane-1,2-diols <BO>1</BO>, reacting with 4-biphenylboronic acid <BO>2</BO>, form the conformationally defined boronates <BO>3</BO> where the aryl and biphenyl chromophores assume a fixed and known relative disposition. These chromophores thus define an exciton coupled system, whose chirality (revealed by the sign of the biphenyl CD band at 260 nm) allows an unambiguous assignment of the absolute configuration of the stereogenic center. This approach provides the hitherto unreported absolute configuration of diols <BO>1c</BO><BO>−</BO><BO>f</BO>.