Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system

Takanori Shibata, Shiho Yoshida, Yoshikazu Arai, Maiko Otsuka, Kohei Endo

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

A chiral iridium complex catalyzed a consecutive and enantioselective [2+2+2] cycloaddition of polyynes to give axially chiral compounds. Intermolecular reaction of tetraynes, possessing aryl groups on their termini, with protected but-2-yne-1,4-diols gave C2-symmetrical quateraryl compounds. Intramolecular reaction of hexaynes, possessing aryl or alkyl groups on their termini gave C2-symmetrical biaryl compounds. The catalytic synthesis of a pentacene derivative with axial chiralities is also discussed.

Original languageEnglish
Pages (from-to)821-830
Number of pages10
JournalTetrahedron
Volume64
Issue number5
DOIs
Publication statusPublished - 2008 Jan 28

Keywords

  • Axial chirality
  • Biaryls
  • Cycloaddition
  • Enantioselective
  • Iridium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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