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Novel Bifunctional Chiral Urea and Thiourea Derivatives as Organocatalysts: Enantioselective Nitro-Michael Reaction of Malonates and Diketones

  1. José M. Andrés Dr.,
  2. Rubén Manzano,
  3. Rafael Pedrosa Prof. Dr.

Article first published online: 22 APR 2008

DOI: 10.1002/chem.200800633

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 14, Issue 17, pages 5116–5119, June 9, 2008

Additional Information

How to Cite

Andrés, José M., Manzano, R. and Pedrosa, R. (2008), Novel Bifunctional Chiral Urea and Thiourea Derivatives as Organocatalysts: Enantioselective Nitro-Michael Reaction of Malonates and Diketones. Chem. Eur. J., 14: 5116–5119. doi: 10.1002/chem.200800633

Author Information

  1. Centro de Innovación en Química y Materiales Avanzados (CINQUIMA) and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011 Valladolid, Spain, Fax: (+34) 983423211

Publication History

  1. Issue published online: 29 MAY 2008
  2. Article first published online: 22 APR 2008
  3. Manuscript Received: 3 APR 2008

Funded by

  • DGICYT. Grant Number: CTQ2005-01191/BQU
  • Junta de Castilla y León. Grant Number: project VA025A06

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Keywords:

  • asymmetric catalysis;
  • asymmetric synthesis;
  • Michael addition;
  • organocatalysis;
  • thioureas
Thumbnail image of graphical abstract

Novel chiral ureas and thioureas derived form natural α-amino acids have been prepared and tested as bifunctional organocatalysts in enantioselective nitro-Michael additions (see scheme). The reactions occurred with excellent chemical yields and up to 99 % ee.

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