Synthesis and Stereochemistry of Optically Active Selenoxides

Abstract

Some optically active diaryl selenoxides stabilized by bulky oitho substituents such as isopropyl or t-butyl group were obtained by fractionary recrystallization or by chromatographic resolutions. Optically active alkyl aryl selenoxides were synthesized by asymmetric oxidation of corresponding selenides under Sharpless oxidation conditions The absolute configurations of these optically active selenoxides were determined by X-ray diffraction and circular dichroism spectra. The rate of racemization of the optically active selenoxide under several conditions were investigated, and the mechanism involving achiral hydrate was clarified by H218Ostudies. © 1990, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.