Allylic and propargylic phenyl selenide oxygenation by cyclohexanone oxygenase: [2,3]-sigmatraopic rearrangement of the enzyme-generated selenoxide
Abstract
Enzymic oxidation of propargyloic and allylic selenides has been carried out and the resulting selenoxides found to readily undergo 2,3-sigmatropic rearrangement; the propargylic product undergoes fragmentation while the allylic product yields racemic alcohols.