Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts

Eiji Yamamoto, Daichi Gokuden, Ayano Nagai, Takashi Kamachi, Kazunari Yoshizawa, Akiyuki Hamasaki, Tamao Ishida, Makoto Tokunaga

研究成果: ジャーナルへの寄稿記事

30 引用 (Scopus)

抄録

Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

元の言語英語
ページ(範囲)6178-6181
ページ数4
ジャーナルOrganic Letters
14
発行部数24
DOI
出版物ステータス出版済み - 12 21 2012

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Protonation
Ketones
ketones
esters
Condensation
Esters
condensation
catalysts
Catalysts

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts. / Yamamoto, Eiji; Gokuden, Daichi; Nagai, Ayano; Kamachi, Takashi; Yoshizawa, Kazunari; Hamasaki, Akiyuki; Ishida, Tamao; Tokunaga, Makoto.

:: Organic Letters, 巻 14, 番号 24, 21.12.2012, p. 6178-6181.

研究成果: ジャーナルへの寄稿記事

Yamamoto, Eiji ; Gokuden, Daichi ; Nagai, Ayano ; Kamachi, Takashi ; Yoshizawa, Kazunari ; Hamasaki, Akiyuki ; Ishida, Tamao ; Tokunaga, Makoto. / Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts. :: Organic Letters. 2012 ; 巻 14, 番号 24. pp. 6178-6181.
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AU - Yamamoto, Eiji

AU - Gokuden, Daichi

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AU - Kamachi, Takashi

AU - Yoshizawa, Kazunari

AU - Hamasaki, Akiyuki

AU - Ishida, Tamao

AU - Tokunaga, Makoto

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AB - Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

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