Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones

Keiichi Komatsuki, Yuta Sadamitsu, Kohei Sekine, Kodai Saito, Tohru Yamada

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.

Original languageEnglish
Pages (from-to)11594-11598
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number38
DOIs
Publication statusPublished - 2017 Sep 11

Fingerprint

Stereochemistry
Cyclization
Carbon Dioxide
Olefins
Carbonates
Carbon dioxide
Silver
Alcohols
Derivatives
Lewis Acids
Catalysts
Acids
Geometry
Alkenes
Substrates
cyclopentenone
propargyl alcohol

Keywords

  • carbon dioxide
  • C−C bond formation
  • electrocyclic reactions
  • silver
  • stereospecific reactions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones. / Komatsuki, Keiichi; Sadamitsu, Yuta; Sekine, Kohei; Saito, Kodai; Yamada, Tohru.

In: Angewandte Chemie - International Edition, Vol. 56, No. 38, 11.09.2017, p. 11594-11598.

Research output: Contribution to journalArticle

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