Enantioselective direct aldol reaction of α-keto esters catalyzed by (Sa)-binam-D-prolinamide under quasi solvent-free conditions

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Title: Enantioselective direct aldol reaction of α-keto esters catalyzed by (Sa)-binam-D-prolinamide under quasi solvent-free conditions
Authors: Viózquez Cámara, Santiago Fidel | Bañón Caballero, Abraham | Guillena, Gabriela | Nájera, Carmen | Gómez Bengoa, Enrique
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: Enantioselective | Aldol | Organocatalisis | Solvent-free
Knowledge Area: Química Orgánica
Issue Date: 23-Mar-2012
Publisher: Royal Society of Chemistry
Citation: VIÓZQUEZ, Santiago F., et al. “Enantioselective direct aldol reaction of α-keto esters catalyzed by (Sa)-binam-D-prolinamide under quasi solvent-free conditions”. Organic & Biomolecular Chemistry. Vol. 10, Issue 20 (2012). ISSN 1477-0520, pp. 4029-4035
Abstract: (Sa)-Binam-D-prolinamide (20 mol%), instead of (Sa)-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between α-keto esters as electrophiles and alkyl and α-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary γ-keto α-hydroxyesters with up to 92% ee.
Sponsor: This research was supported by the Ministerio de Ciencia e Innovación (MICINN: Projects CTQ2007-62771/BQU, CTQ2010-20387, and Consolider Ingenio2010 CSD2007-00006,), FEDER, the Generalitat Valenciana (Project PROMETEO/2009/039), and the EU (ORCA action CM0905). A.B.-C. thanks the Spanish MICINN for a predoctoral fellowship (FPU AP2009-3601).
URI: http://hdl.handle.net/10045/23276
ISSN: 1477-0520 (Print) | 1477-0539 (Online)
DOI: 10.1039/C2OB25224D
Language: eng
Type: info:eu-repo/semantics/article
Peer Review: si
Publisher version: http://dx.doi.org/10.1039/C2OB25224D
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