Iridium complex-catalyzed highly enantio- and diastereoselective [2+2+2] cycloaddition for the synthesis of axially chiral teraryl compounds

Takanori Shibata, Takayoshi Fujimoto, Kazuhisa Yokota, Kentaro Takagi

Research output: Contribution to journalArticle

166 Citations (Scopus)

Abstract

An asymmetric [2+2+2] cycloaddition of an α,ω-diyne, possessing ortho-substituted aryl groups on its terminus, and a monoalkyne with oxygen functionalities gave various axially chiral teraryl compounds. The coupling proceeded with extremely high enantio- (>99.5% ee) and diastereoselectivities (dl/meso = >95/5) when catalyzed by an iridium-chiral phosphine complex. As the products were readily transformed into diol compounds by deprotection without racemization, the present procedure provides access to a new chiral pool of diol compounds with C2 symmetry.

Original languageEnglish
Pages (from-to)8382-8383
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number27
DOIs
Publication statusPublished - 2004 Jul 14

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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