(R)-3,5-diCF₃-SYNPHOS and (R)-p-CF₃-SYNPHOS, Electron-Poor Diphosphines for Efficient Room Temperature Rh-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids

Farouk Berhal, Olivier Esseiva, Charles-Henri Martin, Hitoshi Tone, Jean-Pierre Genet, Tahar Ayad and Virginie Ratovelomanana-Vidal*

*Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France, Email: virginie-vidalchimie-paristech.fr

F. Berhal, O. Esseiva, C.-H. Martin, H. Tone, J.-P. Genet, T. Ayad, V. Ratovelomanana-Vidal, Org. Lett., 2011, 13, 2806-2809.

DOI: 10.1021/ol200495a

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Abstract

Two new atropisomeric electron-poor chiral diphosphine ligand analogues of SYNPHOS were prepared, that allow a highly performant Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds at room temperature.

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Key Words

1,4-addition, cyclohexanones

ID: J54-Y2011-1520

(R)-3,5-diCF3-SYNPHOS and (R)-p-CF3-SYNPHOS, Electron-Poor Diphosphines for Efficient Room Temperature Rh-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids

Farouk Berhal, Olivier Esseiva, Charles-Henri Martin, Hitoshi Tone, Jean-Pierre Genet, Tahar Ayad and Virginie Ratovelomanana-Vidal*

(R)-3,5-diCF₃-SYNPHOS and (R)-p-CF₃-SYNPHOS, Electron-Poor Diphosphines for Efficient Room Temperature Rh-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids