Decarboxylative Nazarov Cyclization-Based Chirality Transfer for Asymmetric Synthesis of 2-Cyclopentenones

Keiichi Komatsuki, Akane Kozuma, Kodai Saito, Tohru Yamada

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Asymmetric synthesis of 2-cyclopentenones was achieved by chirality transfer based on Lewis acid catalyzed decarboxylative Nazarov cyclization of optically active cyclic enol carbonates, which are prepared by silver-catalyzed carbon dioxide incorporation into optically pure propargyl alcohols. The stereochemistry at the 4,5-positions of the 2-cyclopentenones was cleanly constructed by reflecting the stereochemistry of the starting materials. This method could be applied to various substrates to obtain the corresponding products in high yields with highly efficient chirality transfer.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusAccepted/In press - 2019 Jan 1

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Stereochemistry
Chirality
Cyclization
stereochemistry
chirality
Lewis Acids
Carbonates
synthesis
Silver
Carbon Dioxide
carbon dioxide
carbonates
alcohols
silver
acids
Substrates
products
cyclopentenone
propargyl alcohol

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Decarboxylative Nazarov Cyclization-Based Chirality Transfer for Asymmetric Synthesis of 2-Cyclopentenones. / Komatsuki, Keiichi; Kozuma, Akane; Saito, Kodai; Yamada, Tohru.

In: Organic Letters, 01.01.2019.

Research output: Contribution to journalArticle

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