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.
Catalytic, Highly Enantioselective, Direct Amination of β-Ketoesters†
Article first published online: 26 MAR 2003
© 2002 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 42, Issue 12, pages 1367–1369, March 28, 2003
How to Cite
Marigo, M., Juhl, K. and Jørgensen, K. A. (2003), Catalytic, Highly Enantioselective, Direct Amination of β-Ketoesters. Angew. Chem. Int. Ed., 42: 1367–1369. doi: 10.1002/anie.200390350
- Issue published online: 26 MAR 2003
- Article first published online: 26 MAR 2003
- Manuscript Received: 28 NOV 2002
- asymmetric catalysis;
- synthetic methods
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).