Highly enantioselective construction of a chiral spirocyclic structure by the [2 + 2 + 2] cycloaddition of diynes and exo-methylene cyclic compounds

Kyoji Tsuchikama, Yusuke Kuwata, Takanori Shibata

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

The enantioselective [2 + 2 + 2] cycloaddition of 1,6-diynes with α-methylene lactones and cyclic ketones gave various chiral spirocyclic compounds. The reaction proceeded with high enantioselectivity when the rhodium-xylylBINAP complex was used as a chiral catalyst. Not only exo-methylene cyclic compounds but also exo-methylene acyclic compounds could be used as coupling partners for diynes. The present protocol provides access to a new chiral library possessing a quaternary carbon center, including a spirocyclic system.

Original languageEnglish
Pages (from-to)13686-13687
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number42
DOIs
Publication statusPublished - 2006 Oct 25

ASJC Scopus subject areas

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

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