A novel preparation of chiral (Z)-O-alkyl enol ethers from alkenylselenonium salts

Abstract

The reactions of alkenylselenonium salts with chiral secondary alkoxides afforded chiral (Z)-O-alkyl enol ethers in good yields and, especially in the case of sterically hindered secondary cyclic alcohols, the best results were obtained from reactions of dimethylalkenylselenonium salt 7b with alkoxides prepared from PhLi and the corresponding alcohols in THF at –78 °C.