On the development of catalytic carba-6π electrocyclizations

Lee M. Bishop, Russell E. Roberson, Robert G. Bergman, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Hexatriene substrates substituted in the 2-position with carbonyl groups were studied in the context of catalytic 6pi; electrocyclizations. The nature of the carbonyl group and the substitution pattern on the hexatriene have significant effects on the ability of these substrates to succumb to catalysis. A novel 2-formyl hexatriene dimerization was observed. The first example of a catalytic asymmetric carba-6pi; electrocyclization is reported along with the discovery of an unusual kinetic resolution via a catalytic photochemical electrocyclic ring-opening.

Original languageEnglish (US)
Article numberC03210SS
Pages (from-to)2233-2244
Number of pages12
JournalSynthesis
Issue number13
DOIs
StatePublished - 2010

Keywords

  • Electrocyclic reactions
  • asymmetric catalysis
  • catalysis
  • dimerization
  • kinetic resolution

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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  • Cite this

    Bishop, L. M., Roberson, R. E., Bergman, R. G., & Trauner, D. (2010). On the development of catalytic carba-6π electrocyclizations. Synthesis, (13), 2233-2244. [C03210SS]. https://doi.org/10.1055/s-0029-1218812