Enantioselective intramolecular [2 + 2 + 2] cycloaddition of 1,4-diene-ynes: A new approach to the construction of quaternary carbon stereocenters

Takanori Shibata, Yu Ki Tahara

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

The intramolecular [2 + 2 + 2] cycloaddition of various 1,4-diene-ynes was examined using a chiral rhodium catalyst. In the case of 1,4-diene-ynes with a substituent at the 2-position of the 1,4-diene moiety, tricyclic compounds possessing a strained bicyclo[2.2.1]heptene skeleton with two quaternary carbon stereocenters were obtained in high enantiomeric excess. On the other hand, in the case of 1,4-diene-ynes with no substituent at this position, bicyclic cyclohexa-1,3-dienes with a quaternary carbon stereocenter were obtained probably by carbon-carbon bond cleavage of the reaction intermediate.

Original languageEnglish
Pages (from-to)11766-11767
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number36
DOIs
Publication statusPublished - 2006 Sep 13

ASJC Scopus subject areas

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

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