Synthesis and Chiroptical Properties of a Chiral Isotopologue of syn-Cryptophane-B

J Org Chem. 2023 Apr 7;88(7):4829-4832. doi: 10.1021/acs.joc.2c03101. Epub 2023 Mar 20.

Abstract

We report the synthesis and absolute configuration (AC) of a chiral isotopologue of syn-cryptophane-B. Low chiral signatures were measured by polarimetry and electronic circular dichroism, whereas most significant chiroptical effects were observed by vibrational circular dichroism (VCD) and Raman optical activity (ROA). The comparison of experimental VCD and ROA spectra with those predicted by DFT calculations allows the determination of the AC of the two enantiomers as (-)589-MP-syn-2 and (+)589-PM-syn-2.