Acid-catalyzed Nazarov reaction controlled by β-alkoxy groups

Mitsuru Shindo, Kentaro Yaji, Taisuke Kita, Kozo Shishido

Research output: Contribution to journalArticle

17 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 languageEnglish
Pages (from-to)1096-1100
Number of pages5
JournalSynlett
Issue number7
DOIs
Publication statusPublished - Apr 24 2007

Fingerprint

Regioselectivity
Acids
Ketones
Esters
Stabilization
Catalysts
Substrates
alkoxyl radical
1,3-butadiene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Acid-catalyzed Nazarov reaction controlled by β-alkoxy groups. / Shindo, Mitsuru; Yaji, Kentaro; Kita, Taisuke; Shishido, Kozo.

In: Synlett, No. 7, 24.04.2007, p. 1096-1100.

Research output: Contribution to journalArticle

Shindo, Mitsuru ; Yaji, Kentaro ; Kita, Taisuke ; Shishido, Kozo. / Acid-catalyzed Nazarov reaction controlled by β-alkoxy groups. In: Synlett. 2007 ; No. 7. pp. 1096-1100.
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