Determination of the absolute configurations of isotopically chiral molecules using vibrational circular dichroism (VCD) spectroscopy: the isotopically chiral sulfoxide, perdeuteriophenyl-phenyl-sulfoxide

摘要

The (+) and (-) enantiomers of the isotopically chiral sulfoxide, perdeuteriophenyl-phenyi-sulfoxide, 1, have been synthesized by the reaction of the diastereomers of O-menthyl benzenesulfinate with C6D5MgBr. Their absolute configurations have been determined by comparison of the vibrational circular dichroism (VCD) spectra of (R)-1 and (S)-1, predicted using ab initio DFT, to the experimental VCD spectrum of 1. The absolute configuration of 1 is shown to be (S)(+)1(R)(-). This is the first application of VCD to the determination of the absolute configuration of an isotopically chiral sulfoxide. (c) 2008 Elsevier Ltd. All rights reserved.