Acid-catalyzed Nazarov reaction controlled by β-alkoxy groups

Mitsuru Shindo; Kentaro Yaji; Taisuke Kita; Kozo Shishido

doi:10.1055/s-2007-973900

Acid-catalyzed Nazarov reaction controlled by β-alkoxy groups

Mitsuru Shindo, Kentaro Yaji, Taisuke Kita, Kozo Shishido

Department of Fundamental Organic Chemistry

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

19 Citations (Scopus)

Abstract

Acid-catalyzed Nazarov reaction of β-alkoxy divinyl ketones providing 5-oxycyclopent-2-enones has been developed. The effects of the β-alkoxy group on the catalyst efficiency and the regioselectivity are based on the stabilization of the intermediates and the spontaneous elimination of the group followed by trapping. The substrates are easily accessible using the torquoselective olefination of esters with ynolates.

Original language	English
Pages (from-to)	1096-1100
Number of pages	5
Journal	Synlett
Issue number	7
DOIs	https://doi.org/10.1055/s-2007-973900
Publication status	Published - Apr 24 2007

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-2007-973900

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abstract = "Acid-catalyzed Nazarov reaction of β-alkoxy divinyl ketones providing 5-oxycyclopent-2-enones has been developed. The effects of the β-alkoxy group on the catalyst efficiency and the regioselectivity are based on the stabilization of the intermediates and the spontaneous elimination of the group followed by trapping. The substrates are easily accessible using the torquoselective olefination of esters with ynolates.",

author = "Mitsuru Shindo and Kentaro Yaji and Taisuke Kita and Kozo Shishido",

year = "2007",

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AU - Yaji, Kentaro

AU - Kita, Taisuke

AU - Shishido, Kozo

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N2 - Acid-catalyzed Nazarov reaction of β-alkoxy divinyl ketones providing 5-oxycyclopent-2-enones has been developed. The effects of the β-alkoxy group on the catalyst efficiency and the regioselectivity are based on the stabilization of the intermediates and the spontaneous elimination of the group followed by trapping. The substrates are easily accessible using the torquoselective olefination of esters with ynolates.

AB - Acid-catalyzed Nazarov reaction of β-alkoxy divinyl ketones providing 5-oxycyclopent-2-enones has been developed. The effects of the β-alkoxy group on the catalyst efficiency and the regioselectivity are based on the stabilization of the intermediates and the spontaneous elimination of the group followed by trapping. The substrates are easily accessible using the torquoselective olefination of esters with ynolates.

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Acid-catalyzed Nazarov reaction controlled by β-alkoxy groups

Abstract

All Science Journal Classification (ASJC) codes

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