Solvent-free asymmetric direct aldol reactions organocatalysed by recoverable (Sa)-binam-L-prolinamide
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Title: | Solvent-free asymmetric direct aldol reactions organocatalysed by recoverable (Sa)-binam-L-prolinamide |
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Authors: | Guillena, Gabriela | Hita López, María del Carmen | Nájera, Carmen | Viózquez Cámara, Santiago Fidel |
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 |
Issue Date: | 27-Sep-2007 |
Publisher: | Elsevier |
Citation: | GUILLENA TOWNLEY, Gabriela, et al. "Solvent-free asymmetric direct aldol reactions organocatalysed by recoverable (Sa)-binam-L-prolinamide". Tetrahedron: Asymmetry. Vol. 18, Issue 19 (27 Sept. 2007). ISSN 0957-4166, pp. 2300-2304 |
Abstract: | The combination of (Sa)-binam-L-Pro (5 mol %) and benzoic acid (10 mol %) was used as catalysts in the direct aldol reaction between different aliphatic ketones and 4-nitrobenzaldehyde under solvent-free reaction conditions. Three different procedures are assayed: magnetic stirring (method A), magnetic stirring after previous dissolution in THF and evaporation (method B), and ball mill technique (method C), methods A and B being the simplest. These reaction conditions allowed us to reduce the amount of required ketone to 2 equiv to give the aldol product in similar reaction times and regio-, diastero-, and enantioselectivities than in organic or aqueous solvents. |
Sponsor: | This work was financially supported by the Dirección General de Investigación of the Ministerio de Educación y Ciencia of Spain (Grant CTQ2004-00808/BQU and Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (Grant CTIOIB/2002/320, GRUPOS03/134 and GV05/157) and the University of Alicante (GRJ06-05). |
URI: | http://hdl.handle.net/10045/2508 |
ISSN: | 0957-4166 |
DOI: | 10.1016/j.tetasy.2007.09.020 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1016/j.tetasy.2007.09.020 |
Appears in Collections: | INV - DAPSO - Artículos INV - PCSO - Artículos de Revistas INV - SINTAS - Artículos de Revistas INV - CESO - Artículos de Revistas |
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TETASY56868-1.pdf | Versión final (acceso restringido) | 285,07 kB | Adobe PDF | Open Request a copy |
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