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

2 Citations (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
Pages (from-to)6628-6632
Number of pages5
JournalOrganic Letters
Volume21
Issue number17
DOIs
Publication statusPublished - 2019 Sep 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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