Chiral sulfur-reagents for the preparation of optically active epoxides

Article abstract of DOI:10.1016/S0040-4020(01)88764-0

Acyclic chiral sulfides which could be easily synthesized in both enantiomeric forms leading to poor yields and/or to racemic epoxides, Eliel's oxathiane reagent was used and proved to provide chiral trans diarylepoxides in high yield (70-80%) and enantiomeric purities up to 70-100%, with no rearrangement problems. It was also found that phase-transfer conditions were the easiest and the most efficient for these reactions.