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Copper-Catalyzed Enantioselective Conjugate Addition of Grignard Reagents to α,β-Unsaturated Esters

Authors

  • Fernando López Dr.,

    1. Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • Syuzanna R. Harutyunyan Dr.,

    1. Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • Auke Meetsma,

    1. Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • Adriaan J. Minnaard Dr.,

    1. Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • Ben L. Feringa Prof. Dr.

    1. Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • Financial support from the Dutch Ministry of Economic Affairs under the EET Scheme (grant nos. EETK97107 and EETK99104) and the Sixth Framework Programme of the European Community (Marie Curie Intra-European Fellowship to F.L.; contract no: MEIF-CT-2004-009767) is gratefully acknowledged. We thank T. D. Tiemersma-Wegman for technical support (GC and HPLC) and Dr. W. R. Browne for valuable discussions. We are grateful to Dr. H.-U. Blaser (Solvias, Basel) for a generous gift of josiphos ligands.

Abstract

original image

Stabile zweikernige Cu-Komplexe katalysieren die konjugierte Addition billiger und einfach zugänglicher Grignard-Reagentien an acyclische α,β-ungesättigte Ester. Auf diese Art werden die entsprechenden β-substituierten optisch aktiven Ester in hohen Ausbeuten und mit ausgezeichneten Enantioselektivitäten erhalten (siehe Schema). R3=Cyclohexyl, R4=Ph oder R3=Ph, R4=Cyclohexyl.

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