Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3Z,9Z)-1,2,518-Dithiadiazecine-6,7(5H,8H)-dione Series

作者：Risso Vesna; Farran Daniel^*; Javierre Guilhem; Naubron Jean Valere; Giorgi Michel; Piras Patrick; Jean Marion; Vanthuyne Nicolas; Fruttero Roberta; Lorcy Dominique; Roussel Christian^*

来源：Journal of Organic Chemistry, 2018, 83(15): 7566-7573.

DOI：10.1021/acs.joc.8b01009

For the first time, chirality in (3Z,9Z)-1,2,5,8-dithiadiazecine-6,7(SH,8H)-dione series was recognized. Enantiomers of the 4,9-dimethyl-5,8-diphenyl analogue were isolated at room temperature, and their thermal stability was determined. X-ray crystallography confirmed the occurrence of a pair of enantiomers in the crystal. Absolute configurations were assigned by comparing experimental and calculated vibrational/electronic circular dichroism spectra of isolated enantiomers. A distorted tesseract (four-dimensional hypercube) was used to visualize the calculated enantiomerization process, which requires the rotation around four chirality axes. Conformers of higher energy as well as several concurrent pathways of similar energies were revealed.

• 出版日期2018-8-3