American Chemical Society
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Palladium-Catalyzed Synthesis of Tetrahydrofurans from γ-Hydroxy Terminal Alkenes:  Scope, Limitations, and Stereoselectivity

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journal contribution
posted on 2005-04-15, 00:00 authored by Michael B. Hay, Alison R. Hardin, John P. Wolfe
A new, stereoselective synthesis of substituted tetrahydrofurans via Pd-catalyzed reactions of aryl and vinyl bromides with γ-hydroxy terminal alkenes is described. This transformation affords trans-2,5- and trans-2,3-disubstituted tetrahydrofurans with up to >20:1 dr. This methodology also provides access to bicyclic and spirocyclic tetrahydrofuran derivatives in good yield with 10−20:1 dr. The scope and limitations of these transformations are discussed in detail, as are the effect of substrate sterics and electronics on yield and stereoselectivity. A proposed mechanism of these transformations is presented along with a model that rationalizes the stereochemical outcome of the reactions.