Mechanism of gold-catalyzed cycloisomerization of enynyl esters

Andrea Correa*, Luigi Cavallo

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapterpeer-review

Abstract

A theoretical study on the Au-catalyzed cycloisomerization of a branched dienyne possessing an acetate at the propargylic position is presented. The peculiar architecture of the dienyne precursor, exhibiting both a 1,6- and a 1,5-enyne skeleton, leads, in the presence of alkynophilic gold catalysts, to a mixture of bicyclic compounds. DFT calculations are presented that rationalize in full THE manifold of reactions that lead to the different products.

Original languageEnglish (US)
Title of host publicationGreen Metathesis Chemistry
Subtitle of host publicationGreat Challenges in Synthesis, Catalysis and Nanotechnology
PublisherSpringer Verlag
Pages293-303
Number of pages11
ISBN (Print)9789048134311
DOIs
StatePublished - 2010

Publication series

NameNATO Science for Peace and Security Series A: Chemistry and Biology
ISSN (Print)1874-6489

Keywords

  • Allenes
  • Cycloisomerization
  • Density functional theory calculations
  • Enynes
  • Gold catalysis
  • Homogeneous catalysis
  • Propargylic esters

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology (miscellaneous)
  • Safety, Risk, Reliability and Quality

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