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


Autoria(s): Navarro Moles, Fernando Javier; Guillena, Gabriela; Nájera Domingo, Carmen
Contribuinte(s)

Universidad de Alicante. Departamento de Química Orgánica

Universidad de Alicante. Instituto Universitario de Síntesis Orgánica

Catálisis Estereoselectiva en Síntesis Orgánica (CESO)

Síntesis Asimétrica (SINTAS)

Data(s)

03/03/2015

03/03/2015

20/01/2015

Resumo

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).

Identificador

Synlett. 2015, 26(5): 656-660. doi:10.1055/s-0034-1379969

0936-5214 (Print)

1437-2096 (Online)

http://hdl.handle.net/10045/45430

10.1055/s-0034-1379969

A7693926

Idioma(s)

eng

Publicador

Georg Thieme Verlag

Relação

http://dx.doi.org/10.1055/s-0034-1379969

Direitos

© Georg Thieme Verlag Stuttgart New York. http://www.thieme-connect.com/ejournals/toc/synlett

info:eu-repo/semantics/openAccess

Palavras-Chave #Methylglyoxal #Organocatalysis #Aldol #Prolinamide #Aqueous conditions #Química Orgánica
Tipo

info:eu-repo/semantics/article