Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants.
Fiche publication
Date publication
octobre 2006
Auteurs
Membres identifiés du Cancéropôle Est :
Dr WAGNER Alain
Tous les auteurs :
Silva F, Reiter M, Mills-Webb R, Sawicki M, Klar D, Bensel N, Wagner A, Gouverneur V
Lien Pubmed
Résumé
A novel palladium(II)-catalyzed oxy-carbopalladation process was developed allowing for the orchestrated union of hydroxy ynones with ethyl acrylate, two electron-deficient reactants. With beta-hydroxy ynones, this cascade Wacker-Heck process gave access to highly functionalized tri- or tetrasubstituted dihydropyranones featuring an unusual dienic system. For diastereomerically pure and for enantioenriched beta-hydroxyynones, these reactions proceed without affecting the stereochemical integrity of the existing stereocenters. In addition, tetrasubstituted furanones can be prepared when alpha-hydroxyynones and ethyl acrylate are used as starting materials. The dihydropyranones and furanones obtained upon cyclization are novel compounds, but structurally related carbohydrate derivatives featuring a similar dienic system have been used as starting materials for the construction of polyannulated products, suggesting that these cascade Pd(II)-mediated oxidative heterocyclizations are of value for various synthetic applications.
Référence
J Org Chem. 2006 Oct 27;71(22):8390-4.