Diastereoselective Spiroannulation of Phenolic Derivatives: Effect of Steric Hindrance on the Diastereoselectivity

  •  Guy Plourde    
  •  Lyndia Susag    


This study was aimed at determining the effect, if any, that steric factors may have on the diastereoselectivity in the spiroannulation of simple phenols. A series of phenols bearing different size substituents ortho to the phenolic hydroxyl were synthesized and spiroannulated to the corresponding spiroethers in good to excellent yields (76-94%). However, the diastereoselectivity of the reaction remain mostly unchanged suggesting that stereoelectronic rather then steric factors influence the diastereoselectivity in this reaction.

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  • ISSN(Print): 1916-9698
  • ISSN(Online): 1916-9701
  • Started: 2009
  • Frequency: semiannual

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