Journal of Organic Chemistry p. 2981 - 2987 (1985)
Update date:2022-08-05
Topics:
Zoretic, Phillip A.
Chambers, Robert J.
Marbury, Gordon D.
Riebiro, Anthony A.
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.
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