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Synfacts 2010(6): 0677-0677  
DOI: 10.1055/s-0029-1219860
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tetrahydrofurans by Diastereoselective Carboetherification

Contributor(s): Mark Lautens, Stephen G. Newman
A. F. Ward, J. P. Wolfe*
University of Michigan, Ann Arbor, USA
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Publikationsdatum:
20. Mai 2010 (online)

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Significance

Polysubstituted tetrahydrofurans are commonly found in natural products and pharmaceuticals. Building on previous work with simpler alkenes (see Review below), the authors present an intramolecular palladium-catalyzed carboetherification to produce tetrahydrofurans containing multiple stereocenters. The use of S-Phos as a ligand was crucial for obtaining high ­diastereoselectivity.

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