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

Fingerprint

Dimerization
Substrates
Catalysis
Substitution reactions
Kinetics

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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

On the development of catalytic carba-6π electrocyclizations. / Bishop, Lee M.; Roberson, Russell E.; Bergman, Robert G.; Trauner, Dirk.

In: Synthesis, No. 13, C03210SS, 2010, p. 2233-2244.

Research output: Contribution to journalArticle

Bishop, LM, Roberson, RE, Bergman, RG & Trauner, D 2010, 'On the development of catalytic carba-6π electrocyclizations', Synthesis, no. 13, C03210SS, pp. 2233-2244. https://doi.org/10.1055/s-0029-1218812
Bishop LM, Roberson RE, Bergman RG, Trauner D. On the development of catalytic carba-6π electrocyclizations. Synthesis. 2010;(13):2233-2244. C03210SS. https://doi.org/10.1055/s-0029-1218812
Bishop, Lee M. ; Roberson, Russell E. ; Bergman, Robert G. ; Trauner, Dirk. / On the development of catalytic carba-6π electrocyclizations. In: Synthesis. 2010 ; No. 13. pp. 2233-2244.
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