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. 2005 Apr 15;70(8):3099-107.
doi: 10.1021/jo050022+.

Palladium-catalyzed synthesis of tetrahydrofurans from gamma-hydroxy terminal alkenes: scope, limitations, and stereoselectivity

Michael B Hay  1 , Alison R Hardin, John P Wolfe
Affiliations

Palladium-catalyzed synthesis of tetrahydrofurans from gamma-hydroxy terminal alkenes: scope, limitations, and stereoselectivity

Michael B Hay et al. J Org Chem. .

Abstract

A new, stereoselective synthesis of substituted tetrahydrofurans via Pd-catalyzed reactions of aryl and vinyl bromides with gamma-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.

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Figures

Figure 1
Figure 1. Proposed Catalytic Cycle
Figure 2
Figure 2. Proposed Insertion Mechanism
Figure 3
Figure 3. Stereochemistry of 2,5-Disubstituted Tetrahydrofuran Products
Figure 4
Figure 4. Stereochemistry of 2,3-Disubstituted Tetrahydrofuran Products
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