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Pedrosa R, Andrés JM, Manzano R, et al. Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water. Org Biomol Chem. 2010;9(3):935-40doi: 10.1039/c0ob00688b.
Pedrosa, R., Andrés, J. M., Manzano, R., Román, D., & Téllez, S. (2011). Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water. Organic & biomolecular chemistry, 9(3), 935-40. https://doi.org/10.1039/c0ob00688b
Pedrosa, Rafael, et al. "Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water." Organic & biomolecular chemistry vol. 9,3 (2011): 935-40. doi: https://doi.org/10.1039/c0ob00688b
Pedrosa R, Andrés JM, Manzano R, Román D, Téllez S. Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water. Org Biomol Chem. 2011 Feb 07;9(3):935-40. doi: 10.1039/c0ob00688b. Epub 2010 Dec 10. PMID: 21152568.
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Org Biomol Chem. 2011 Feb 07;9(3):935-40. doi: 10.1039/c0ob00688b. Epub 2010 Dec 10.

Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water.

Organic & biomolecular chemistry

Rafael Pedrosa, José M Andrés, Rubén Manzano, David Román, Silvia Téllez

Affiliations

  1. Instituto CINQUIMA and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr Mergelina s/n, 47011, Valladolid, Spain. [email protected]

PMID: 21152568 DOI: 10.1039/c0ob00688b

Abstract

Four novel benzamido-functionalized prolinamides have been prepared and tested as organocatalysts for enantioselective aldol reaction of aldehydes and cyclic ketones in water. In particular, prolinamide derived from achiral ethylene diamine was the best catalyst leading to anti aldols in excellent diastereomeric (up to 98/2) and enantiomeric (up to 99/1) ratios, thereby showing that lateral amide functionalities might be a key issue for facilitating "in water" chemistry. These catalysts are cheaper and easier to prepare than those previously described.

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