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, cilt.80, sa.11, ss.5494-5506, 2015 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 80 Sayı: 11
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1021/acs.joc.5b00382
  • Dergi Adı: Journal of Organic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5494-5506
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

© 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.