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

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

doi:10.1039/C39860000528

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

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

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

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 language	English (US)
Pages (from-to)	528-530
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	7
DOIs	https://doi.org/10.1039/C39860000528
State	Published - 1986
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

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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 Branchaud, {Bruce P.} and Chen, {Y. C.Jack} and Christopher Walsh",

year = "1986",

doi = "10.1039/C39860000528",

language = "English (US)",

pages = "528--530",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Royal Society of Chemistry",

number = "7",

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TY - JOUR

T1 - Allylic and propargylic phenyl selenide oxygenation by cyclohexanone oxygenase

T2 - [2,3]-sigmatraopic rearrangement of the enzyme-generated selenoxide

AU - Latham, John A.

AU - Branchaud, Bruce P.

AU - Chen, Y. C.Jack

AU - Walsh, Christopher

PY - 1986

Y1 - 1986

N2 - 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.

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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U2 - 10.1039/C39860000528

DO - 10.1039/C39860000528

M3 - Article

AN - SCOPUS:37049084179

SN - 0022-4936

SP - 528

EP - 530

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 7

ER -

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

Abstract

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