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Catalytic, Highly Enantioselective, Direct Amination of β-Ketoesters

Authors

  • Mauro Marigo,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
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  • Karsten Juhl Dr.,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
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  • Karl Anker Jørgensen Dr.

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
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  • This work was made possible by a grant from The Danish National Research Foundation and the EU: HMPT-CT-2001-00317. We are grateful to Dr. R. G. Hazell for X-ray crystallographic analysis.

Abstract

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Optically active α-amino acid derivatives were accessed through the direct asymmetric α-amination of α-substituted β-ketoesters 1, catalyzed by chiral CuII–bisoxazoline (BOX) complexes. The reaction proceeds with dibenzyl azodicarboxylate in the presence of only 0.2 mol % of the catalyst to give the desired products 2 in high yield with excellent enantioselectivity (up to 99 % ee).

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