Allylic and propargylic phenyl selenide oxygenation by cyclohexanone oxygenase:[2, 3]-sigmatraopic rearrangement of the enzyme-generated selenoxide

JA Latham, BP Branchaud, YCJ Chen…

Index: Latham, John A.; Branchaud, Bruce P.; Chen, Y.-C. Jack; Walsh, Christopher Journal of the Chemical Society, Chemical Communications, 1986 , # 7 p. 528 - 530

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Citation Number: 11

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.

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