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Synfacts 2009(8): 0878-0878  
DOI: 10.1055/s-0029-1217445
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Etherification in the Synthesis of bis-Tetrahydrofurans

Contributor(s): Mark Lautens, Jane Panteleev
A. F. Ward, J. P. Wolfe*
University of Michigan, Ann Arbor, USA
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

The authors present an efficient protocol for the synthesis of substituted bis-tetrahydrofuran systems 2 and 4. The reactivity utilized has already been extensively explored by the group (see Review below) and this report presents an application of this transformation towards targets with more complexity. While alternative protocols also access bis-tetrahydrofurans from diol starting materials (i.e., J. Wang, B. L. Pagenkopf Org. Lett. 2007, 9, 3703), this method may offer advantages since in situ functionalization of the α-positions in the tetrahydrofuran rings is possible.

Review: J. P. Wolfe Synlett 2008, 2913-2937.