Aqueous Enantioselective Aldol Reaction of Methyl- and Phenylglyoxal Organocatalyzed by N-Tosyl-(S a)-binam-l-prolinamide

• Published in: Synlett
• Main Authors: Navarro Moles, Fernando Javier, Guillena, Gabriela, Nájera, Carmen
• Other Authors: Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Catálisis Estereoselectiva en Síntesis Orgánica (CESO), Síntesis Asimétrica (SINTAS)
• Format: Article in Journal/Newspaper
• Language: English
• Published: Georg Thieme Verlag 2015
• Subjects: Methylglyoxal; Organocatalysis; Aldol; Prolinamide; Aqueous conditions; Química Orgánica; Orca
• Online Access: http://hdl.handle.net/10045/45430; https://doi.org/10.1055/s-0034-1379969

The direct aldol reaction between methylglyoxal (40% aqueous solution) or phenylglyoxal monohydrate and ketones or aldehydes is catalyzed by N-tosyl-(S a)-binam-l-prolinamide to afford the corresponding chiral γ-oxo-β-hydroxy carbonyl compounds, mainly as anti isomers with enantioselectivities up to 97%. This work was financially supported by the Ministerio de Economia y Competitividad (MINECO: Projects: CTQ2010-20387 and Consolider INGENIO CSD2007-0006), FEDER, the Generalitat Valenciana (Prometeo/2009/039), the University of Alicante and the EU (ORCA action CM0905).