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

John A. Latham, Bruce Branchaud, Y. C.Jack Chen, Christopher Walsh

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Enzymic oxidation of propargylic 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.

Original languageEnglish (US)
Pages (from-to)528-530
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number7
DOIs
StatePublished - Jan 1 1986
Externally publishedYes

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Oxygenation
Alcohols
Enzymes
Oxidation
Oxygenases
cyclohexanone oxygenase

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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title = "Allylic and propargylic phenyl selenide oxygenation by cyclohexanone oxygenase: [2,3]-sigmatraopic rearrangement of the enzyme-generated selenoxide",
abstract = "Enzymic oxidation of propargylic 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.",
author = "Latham, {John A.} and Bruce Branchaud and Chen, {Y. C.Jack} and Christopher Walsh",
year = "1986",
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language = "English (US)",
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journal = "Chemical Communications",
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T2 - [2,3]-sigmatraopic rearrangement of the enzyme-generated selenoxide

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AU - Branchaud, Bruce

AU - Chen, Y. C.Jack

AU - Walsh, Christopher

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AB - Enzymic oxidation of propargylic 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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