Optical Resolution of Selenonium Imides Stabilized by an 8-Dimethylamino-1-naphthyl Group

Abstract

Selenonium imides 1 and 2, stabilized by intramolecular coordination of the amino group of 8-dimethylamino-1-naphthyl substituent to the selenium atom, were synthesized. Optically active selenonium imides were obtained by chromatographic resolution on optically active columns and were found to be stable toward racemization both in the solid state and in solution. Absolute configurations of the optically active selenonium imides were assigned on the basis of specific rotations and circular dichroism spectra.

Recent Advances in Organoselenium Chemistry

“…In 2007, Shimizu et al additionally reported the synthesis and optical resolution of selenonium imides bearing an 8-dimethylamino-1-naphthyl group. [114] The selenonium imides were obtained by reaction of the corresponding selenoxides with p-toluenesulfonamide or trifluoromethanesulfonamide. The stable products were isolated in 19 % to 53 % yield and separated by HPLC.…”