BINAM-prolinamides as recoverable catalysts in the direct aldol condensation

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Title: BINAM-prolinamides as recoverable catalysts in the direct aldol condensation
Authors: Guillena, Gabriela | Hita López, María del Carmen | Nájera, Carmen
Research Group/s: Derivados de Aminoácidos y Péptidos en Síntesis Orgánica | Procesos Catalíticos en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: Organocatalysis | Aldol | Enantioselective | Asymmetric synthesis | Amino acids | Proline
Knowledge Area: Química Orgánica
Date Created: 2006
Issue Date: 6-Mar-2006
Publisher: Elsevier
Citation: GUILLENA TOWNLEY, Gabriela; HITA, María del Carmen; NÁJERA DOMINGO, Carmen. "BINAM-prolinamides as recoverable catalysts in the direct aldol condensation". Tetrahedron: Asymmetry. Vol. 17, Issue 5 (6 March 2006). ISSN 0957-4166, pp. 729-733
Abstract: New BINAM-prolinamides were developed and tested as organocatalysts in the direct aldol condensation between aldehydes and several aliphatic ketones. C2-symmetrical (Sa)-BINAM-L-prolinamide gives the best enantioselectivities for this transformation, being recovered and reused after the reaction by simple extractive techniques. The reaction was performed in DMF/H2O at 0 °C to give the aldol products in up to 95% ee for acetone. For 2-butanone, the corresponding iso-regioisomers were regioselectively obtained in up to 96% ee working in DMF at rt. In the case of cyclohexanone, dr up to 10:1 in favour of the anti products, which were obtained in 90–93% ee, was achieved.
Sponsor: This work was financially supported by the Dirección General de Investigación of the Ministerio de Educación y Ciencia of Spain (Grant BQU2001-0724-CO2-01 and CTQ2004-00808/BQU), the Generalitat Valenciana (Grant CTIOIB/2002/320, GRUPOS03/134 and GV05/ 157) and the University of Alicante.
ISSN: 0957-4166
DOI: 10.1016/j.tetasy.2006.02.004
Language: eng
Type: info:eu-repo/semantics/article
Peer Review: si
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