Stereochemistry of Nueleophilic Epoxidation of (S)-2-p-tolylsulfonyl-2-cyclohexenol and O-derivatives

Article abstract of DOI:10.1016/S0040-4039(00)74070-6

Epoxidation of 2-p-tolylsulfonyl-2-cyclohexenol 3 and its OAC (4) and OMOM (5) derivatives with LiOOt-Bu and NaOOH/H₂O with high stereoselectivity to give the syn epoxy alcohols 7-9. The O-triisopropylsilyl derivative (OTIPS, 6) evolves into a 63:37 mixture of syn:anti epoxides. A rationalization of these results, based on the conformational preferences of the starting substrates, is proposed.