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

Guy L Plourde, Lyndia M. 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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DOI: http://dx.doi.org/10.5539/ijc.v3n1p3

International Journal of Chemistry   ISSN 1916-9698 (Print)   ISSN 1916-9701 (Online)

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