Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

Cindy C. Browder; Christopher B. Moss; Matthew B. Kraft; Paige L. Petrucka; Tara S. Morey; Christopher W. Leach; Nicholas C. Gearhart

doi:10.2174/157017811795371476

Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

Cindy C. Browder, Christopher B. Moss, Matthew B. Kraft, Paige L. Petrucka, Tara S. Morey, Christopher W. Leach, Nicholas C. Gearhart

Chemistry and Biochemistry

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

Abstract

An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

Original language	English (US)
Pages (from-to)	229-233
Number of pages	5
Journal	Letters in Organic Chemistry
Volume	8
Issue number	4
DOIs	https://doi.org/10.2174/157017811795371476
State	Published - May 2011

Keywords

Copper-mediated
Cyclization
Isoxazole

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.2174/157017811795371476

Cite this

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title = "Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles",

abstract = "An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.",

keywords = "Copper-mediated, Cyclization, Isoxazole",

author = "Browder, {Cindy C.} and Moss, {Christopher B.} and Kraft, {Matthew B.} and Petrucka, {Paige L.} and Morey, {Tara S.} and Leach, {Christopher W.} and Gearhart, {Nicholas C.}",

year = "2011",

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language = "English (US)",

volume = "8",

pages = "229--233",

journal = "Letters in Organic Chemistry",

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T1 - Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

AU - Browder, Cindy C.

AU - Moss, Christopher B.

AU - Kraft, Matthew B.

AU - Petrucka, Paige L.

AU - Morey, Tara S.

AU - Leach, Christopher W.

AU - Gearhart, Nicholas C.

PY - 2011/5

Y1 - 2011/5

N2 - An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

AB - An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

KW - Copper-mediated

KW - Cyclization

KW - Isoxazole

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VL - 8

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EP - 233

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 4

ER -

Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

Abstract

Keywords

ASJC Scopus subject areas

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