α,β-epoxy vinyl triflates in Pd-catalyzed reactions

Kana Yamamoto, Clayton H. Heathcock

Research output: Contribution to journal › Article

20 Citations (Scopus)

Abstract

(matrix presented) Reactions of steroidal αβ-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd0 into the C-O bond, giving vinylpalladium 12, is faster than formation of the π-allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.

Original languageEnglish
Pages (from-to)1709-1712
Number of pages4
JournalOrganic Letters
Volume2
Issue number12
DOIs
Publication statusPublished - 2000 Jun 15
Externally publishedYes

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Epoxy Compounds
Palladium
Derivatives
epoxy compounds
alkoxides
palladium
insertion
matrices
vinyl triflate

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

α,β-epoxy vinyl triflates in Pd-catalyzed reactions. / Yamamoto, Kana; Heathcock, Clayton H.

In: Organic Letters, Vol. 2, No. 12, 15.06.2000, p. 1709-1712.

Research output: Contribution to journal › Article

Yamamoto, K & Heathcock, CH 2000, 'α,β-epoxy vinyl triflates in Pd-catalyzed reactions', Organic Letters, vol. 2, no. 12, pp. 1709-1712. https://doi.org/10.1021/ol000064e
Yamamoto K, Heathcock CH. α,β-epoxy vinyl triflates in Pd-catalyzed reactions. Organic Letters. 2000 Jun 15;2(12):1709-1712. https://doi.org/10.1021/ol000064e
Yamamoto, Kana ; Heathcock, Clayton H. / α,β-epoxy vinyl triflates in Pd-catalyzed reactions. In: Organic Letters. 2000 ; Vol. 2, No. 12. pp. 1709-1712.
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