Chain-walking strategy for organic synthesis: Catalytic cycloisomerization of 1,n-dienes

Takuya Kochi, Taro Hamasaki, Yuka Aoyama, Junichi Kawasaki, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

76 Citations (Scopus)

Abstract

The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/ hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.

Original languageEnglish
Pages (from-to)16544-16547
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number40
DOIs
Publication statusPublished - 2012 Oct 10

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Chain-walking strategy for organic synthesis: Catalytic cycloisomerization of 1,n-dienes'. Together they form a unique fingerprint.

  • Cite this