Palladium‐Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

نویسندگان

  • Abhijit Sau
  • Ryan Williams
  • Carlos Palo-Nieto
  • Antonio Franconetti
  • Sandra Medina
  • M Carmen Galan
چکیده

Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

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عنوان ژورنال:

دوره 56  شماره 

صفحات  -

تاریخ انتشار 2017