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

doi:10.1021/ol3027363

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

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

32 Citations (Scopus)

Abstract

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).

Original language	English
Pages (from-to)	6178-6181
Number of pages	4
Journal	Organic letters
Volume	14
Issue number	24
DOIs	https://doi.org/10.1021/ol3027363
Publication status	Published - Dec 21 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3027363

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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.

In: Organic letters, Vol. 14, No. 24, 21.12.2012, p. 6178-6181.

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

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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

PY - 2012/12/21

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N2 - 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).

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

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