Stereospecific Synthesis of Secondary Allylic Alcohols: Selenoxide Chemistry

Article abstract of DOI:10.1021/jo00216a035

A stereospecific <2,3> sigmatropic rearrangement of secondary allylic selenoxides as a route to allylic alcohols having a defined stereochemistry is decribed.It has been demonstrated that secondary allylic alcohols react with aryl selenocyanates in the presence of tri-n-butylphosphine with inversion of configuration and that subsequent <2.3> sigmatropic rearrangement of the resulting selenoxides afforded stereospecifically generated allylic alcohol systems.