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

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...

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Bibliographic Details
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
Description
Summary: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).

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