Aqueous organocatalyzed aldol reaction of glyoxylic acid for the enantioselective synthesis of α-hydroxy-γ-keto acids

N-Tosyl-(Sa)-binam-L-prolinamide is an efficient catalyst for the aqueous aldol reaction, between glyoxylic acid, as monohydrate or aqueous solution, and ketones. This reaction led to the formation of chiral α-hydroxy-γ-keto carboxylic acids in high levels of diastereo- and enantioselectivities achi...

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Bibliographic Details
Published in:RSC Advances
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: Royal Society of Chemistry 2013
Subjects:
Organocatalysis
Water
Química Orgánica
Orca
Online Access:http://hdl.handle.net/10045/36098
https://doi.org/10.1039/C3RA46800C
Description
Summary:N-Tosyl-(Sa)-binam-L-prolinamide is an efficient catalyst for the aqueous aldol reaction, between glyoxylic acid, as monohydrate or aqueous solution, and ketones. This reaction led to the formation of chiral α-hydroxy-γ-keto carboxylic acids in high levels of diastereo- and enantioselectivities achieving mainly anti aldol products. This work was financially supported by the Ministerio de Economia y Competitividad (MINECO: Projects: CTQ2010-20387 and Consolider INGENIO CSD2007-0006), the Generalitat Valenciana Prometeo/2009/039, the University of Alicante and the EU (ORCA action CM0905).

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