Absolute Stereochemisty and Chiroptical Properties of 3,3′-Bis(methoxycarbonyl)-9,9′-bianthryl

Abstract

Abstract The axially chiral title compound was enantiomerically resolved by the diastereomer method via the camphorsultamamide of the corresponding dicarboxylic acid. The absolute stereochemistry of the (+)- and (−)-forms ([α]D +32 and −33) was determined by X-ray analysis of one of the diastereomers of the sultamamide to be P and M, respectively, for the helicity about the C9–C9′ bond. The observed CD and UV spectra were reasonably reproduced by the theoretical calculation based on the time-dependent density functional theory (TDDFT). The CD spectrum of the (M)-(−) form features a split curve around 270 nm assignable to the exciton coupling of the β transition and a broad p band peak around 380 nm.