Regioselective oxidation of internal olefins bearing neighboring oxygen functions by means of palladium catalysts. Preparation of β-alkoxy or acetoxy ketones from allyl and homoallyl ethers or esters

Jiro Tsuji, Hideo Nagashima, Kimihiko Hori

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

A new preparative method of β- and γ-alkoxy (acetoxy) ketones, which are important precursors of vinyl ketones and 1,4-diketones, respectively, is presented. With PdCl2/CuCl/O2 or PdCl2/p-benzoquinone catalyst system, internal olefins bearing allylic alkoxy or acetoxy group underwent regioselective oxidation to form the corresponding β-alkoxy or β-acetoxy ketones. Similarly, γ-acetoxy ketones were obtained from homoallyl acetates having internal olefins with high regioselectivity.

Original languageEnglish
Pages (from-to)2679-2682
Number of pages4
JournalTetrahedron Letters
Volume23
Issue number26
DOIs
Publication statusPublished - Jan 1 1982
Externally publishedYes

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Bearings (structural)
Ethers
Palladium
Alkenes
Ketones
Esters
Oxygen
Oxidation
Catalysts
Regioselectivity
Acetates
alkoxyl radical

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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T1 - Regioselective oxidation of internal olefins bearing neighboring oxygen functions by means of palladium catalysts. Preparation of β-alkoxy or acetoxy ketones from allyl and homoallyl ethers or esters

AU - Tsuji, Jiro

AU - Nagashima, Hideo

AU - Hori, Kimihiko

PY - 1982/1/1

Y1 - 1982/1/1

N2 - A new preparative method of β- and γ-alkoxy (acetoxy) ketones, which are important precursors of vinyl ketones and 1,4-diketones, respectively, is presented. With PdCl2/CuCl/O2 or PdCl2/p-benzoquinone catalyst system, internal olefins bearing allylic alkoxy or acetoxy group underwent regioselective oxidation to form the corresponding β-alkoxy or β-acetoxy ketones. Similarly, γ-acetoxy ketones were obtained from homoallyl acetates having internal olefins with high regioselectivity.

AB - A new preparative method of β- and γ-alkoxy (acetoxy) ketones, which are important precursors of vinyl ketones and 1,4-diketones, respectively, is presented. With PdCl2/CuCl/O2 or PdCl2/p-benzoquinone catalyst system, internal olefins bearing allylic alkoxy or acetoxy group underwent regioselective oxidation to form the corresponding β-alkoxy or β-acetoxy ketones. Similarly, γ-acetoxy ketones were obtained from homoallyl acetates having internal olefins with high regioselectivity.

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