Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3 + 2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(-)-Puraquinonic Acid

Miho Oga, Yusei Takamatsu, Akihiro Ogura, Ken Ichi Takao

Research output: Contribution to journalArticlepeer-review

Abstract

A highly stereoselective (3 + 2) cycloaddition for the asymmetric synthesis of versatile cyclopentene compounds containing all-carbon quaternary stereocenters was developed. The phosphine-catalyzed reactions of alkynoates with α-alkylated electron-deficient alkenes bearing Oppolzer's camphorsultam showed high to excellent diastereoselectivities and perfect regioselectivities. The usefulness of this reaction was demonstrated in the concise formal synthesis of (R)-(-)-puraquinonic acid.

Original languageEnglish
Pages (from-to)8788-8795
Number of pages8
JournalJournal of Organic Chemistry
Volume87
Issue number13
DOIs
Publication statusPublished - 2022 Jul 1

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3 + 2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(-)-Puraquinonic Acid'. Together they form a unique fingerprint.

Cite this