Macrolactonization via hydrocarbon oxidation

Kenneth J. Fraunhoffer, Narayanasamy Prabagaran, Lauren E. Sirois, M. Christina White

Research output: Contribution to journalArticle

159 Citations (Scopus)

Abstract

A novel Pd/sulfoxide-catalyzed macrolactonization reaction of linear ω-alkenoic acids is reported that proceeds via serial ligand-catalyzed allylic C-H oxidation. The scope of this macrolactonization appears to be very broad. Aryl, alkyl, and (Z)-α,β-unsaturated acids are all competent nucleophiles for this reaction, with the latter undergoing macrolactonization with no olefin isomerization. High functional group compatibility is observed that includes biologically and medicinally relevant functionality such as ortho-substituted salicylate esters, bis(indoyl)maleimides, and peptides. Evidence is provided to support the hypothesis that macrolactonization proceeds via inner-sphere functionalization from a templated π-allylPd carboxylate intermediate.

Original languageEnglish (US)
Pages (from-to)9032-9033
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number28
DOIs
StatePublished - Jul 19 2006

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sulfoxide
Maleimides
Nucleophiles
Salicylates
Alkenes
Isomerization
Hydrocarbons
Carboxylic acids
Functional groups
Peptides
Olefins
Esters
Ligands
Oxidation
Acids

ASJC Scopus subject areas

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

Cite this

Macrolactonization via hydrocarbon oxidation. / Fraunhoffer, Kenneth J.; Prabagaran, Narayanasamy; Sirois, Lauren E.; White, M. Christina.

In: Journal of the American Chemical Society, Vol. 128, No. 28, 19.07.2006, p. 9032-9033.

Research output: Contribution to journalArticle

Fraunhoffer, Kenneth J. ; Prabagaran, Narayanasamy ; Sirois, Lauren E. ; White, M. Christina. / Macrolactonization via hydrocarbon oxidation. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 28. pp. 9032-9033.
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