Palladium-catalyzed [4 + 2] cycloaddition of o-(silylmethyl)benzyl esters with ketones: An equivalent to oxo-diels-alder reaction of o-xylylenes

Satoshi Ueno, Masakazu Ohtsubo, Ryoichi Kuwano

研究成果: ジャーナルへの寄稿記事

20 引用 (Scopus)

抄録

Figure Presented. o-(Silylmethyl)benzyl carbonates reacted with various electron-deficient ketones in the presence of a palladium catalyst, affording the [4 + 2] cycloaddition products, isochromanes, in high yields. The palladium-catalyzed cycloaddition is equivalent to the oxo-Diels-Alder reaction of o-xylylene with ketones. The regioselectivities were extraordinarily affected by the structures of the o-xylylene precursors and ketones. The unusual regiochemistry may support two competitive reaction pathways in the catalytic reaction.

元の言語英語
ページ(範囲)4332-4334
ページ数3
ジャーナルOrganic Letters
12
発行部数19
DOI
出版物ステータス出版済み - 10 1 2010

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Diels-Alder reactions
Cycloaddition
Cycloaddition Reaction
Palladium
cycloaddition
Ketones
ketones
palladium
esters
Esters
Regioselectivity
Carbonates
carbonates
Electrons
catalysts
Catalysts
products
electrons

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

Palladium-catalyzed [4 + 2] cycloaddition of o-(silylmethyl)benzyl esters with ketones : An equivalent to oxo-diels-alder reaction of o-xylylenes. / Ueno, Satoshi; Ohtsubo, Masakazu; Kuwano, Ryoichi.

:: Organic Letters, 巻 12, 番号 19, 01.10.2010, p. 4332-4334.

研究成果: ジャーナルへの寄稿記事

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abstract = "Figure Presented. o-(Silylmethyl)benzyl carbonates reacted with various electron-deficient ketones in the presence of a palladium catalyst, affording the [4 + 2] cycloaddition products, isochromanes, in high yields. The palladium-catalyzed cycloaddition is equivalent to the oxo-Diels-Alder reaction of o-xylylene with ketones. The regioselectivities were extraordinarily affected by the structures of the o-xylylene precursors and ketones. The unusual regiochemistry may support two competitive reaction pathways in the catalytic reaction.",
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N2 - Figure Presented. o-(Silylmethyl)benzyl carbonates reacted with various electron-deficient ketones in the presence of a palladium catalyst, affording the [4 + 2] cycloaddition products, isochromanes, in high yields. The palladium-catalyzed cycloaddition is equivalent to the oxo-Diels-Alder reaction of o-xylylene with ketones. The regioselectivities were extraordinarily affected by the structures of the o-xylylene precursors and ketones. The unusual regiochemistry may support two competitive reaction pathways in the catalytic reaction.

AB - Figure Presented. o-(Silylmethyl)benzyl carbonates reacted with various electron-deficient ketones in the presence of a palladium catalyst, affording the [4 + 2] cycloaddition products, isochromanes, in high yields. The palladium-catalyzed cycloaddition is equivalent to the oxo-Diels-Alder reaction of o-xylylene with ketones. The regioselectivities were extraordinarily affected by the structures of the o-xylylene precursors and ketones. The unusual regiochemistry may support two competitive reaction pathways in the catalytic reaction.

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