Catalytic enantioselective synthesis of chiral tetraphenylenes: Consecutive inter- and intramolecular cycloadditions of two triynes

Takanori Shibata, Tatsuya Chiba, Hiroyuki Hirashima, Yasunori Ueno, Kohei Endo

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

Triynes having a phenylene-bridged 1,5-diyne moiety were transformed into substituted tetraphenylenes by the title sequence. A cationic Rh-ligand species catalyzed this highly enantioselective reaction. This protocol is a new and easy approach to the construction of the tetraphenylene skeleton and enables an efficient asymmetric synthesis (see scheme; R=H; Z=NTs, C(CO2Me) 2, O).

Original languageEnglish
Pages (from-to)8066-8069
Number of pages4
JournalAngewandte Chemie - International Edition
Volume48
Issue number43
DOIs
Publication statusPublished - 2009 Oct 12

Keywords

  • Alkynes
  • Asymmetric synthesis
  • Chirality
  • Cycloaddition
  • Rhodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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