Volume 54, Issue 45 pp. 13390-13392

Communication

Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans

Brett A. Hopkins,

Brett A. Hopkins

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)

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Zachary J. Garlets,

Zachary J. Garlets

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)

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Prof. Dr. John P. Wolfe,

Corresponding Author

Prof. Dr. John P. Wolfe

[email protected]

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)Search for more papers by this author

Brett A. Hopkins,

Brett A. Hopkins

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)

Search for more papers by this author

Zachary J. Garlets,

Zachary J. Garlets

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)

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Prof. Dr. John P. Wolfe,

Corresponding Author

Prof. Dr. John P. Wolfe

[email protected]

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)

Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA)Search for more papers by this author

First published: 14 September 2015

https://doi.org/10.1002/anie.201506884

Citations: 63

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Graphical Abstract

The construction of enantiomerically enriched tetrahydrofurans is accomplished by asymmetric Pd-catalyzed cross-coupling reactions between γ-hydroxyalkenes and aryl bromides. Use of a palladium catalyst supported by a new TADDOL-derived chiral phosphite ligand provides the tetrahydrofuran products in good yield with up to 96:4 e.r. (see scheme).

Abstract

The Pd-catalyzed coupling of γ-hydroxyalkenes with aryl bromides affords enantiomerically enriched 2-(arylmethyl)tetrahydrofuran derivatives in good yield and up to 96:4 e.r. This transformation was achieved through the development of a new TADDOL/2-arylcyclohexanol-derived chiral phosphite ligand. The transformations are effective with an array of different aryl bromides, and can be used for the preparation of products bearing quaternary stereocenters.

Supporting Information

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Volume54, Issue45

November 2, 2015

Pages 13390-13392

Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans

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Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans

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