Palladium-catalyzed alkoxycarbonylation of conjugated enyne oxiranes: A diastereoselective method for the synthesis of 7-hydroxy-2,3,5-trienoates

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Kuş M., Artok L., AYGÜN M.

Journal of Organic Chemistry, vol.80, no.11, pp.5494-5506, 2015 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 80 Issue: 11
  • Publication Date: 2015
  • Doi Number: 10.1021/acs.joc.5b00382
  • Journal Name: Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5494-5506
  • Dokuz Eylül University Affiliated: Yes

Abstract

© 2015 American Chemical Society.Palladium-catalyzed alkoxycarbonylative 1,5-substitution of conjugated enyne oxiranes provides a diastereoselective route to (E)-configured 7-hydroxy-2,3,5-trienoates. The reactions proceeded in a highly stereoselective manner, possibly through sequential formation of π-allylpalladium and σ-vinylallenyl palladium complexes. The major diastereomeric form of the product is determined by the configuration of the alkenyl moiety of the substrate.