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

22 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

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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