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Synfacts 2009(3): 0325-0325
DOI: 10.1055/s-0028-1087721
DOI: 10.1055/s-0028-1087721
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Proline-Thiourea Self-Assemblies in Aldol Reactions
Ö. Reis, S. Eymur, B. Reis, A. S. Demir*
Middle East Technical University, Ankara, Turkey
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. Februar 2009 (online)
Significance
The proline-thiourea assembly-catalyzed intermolecular aldol reaction of aromatic aldehydes with cyclohexanone is reported. The anti-configured products were obtained in high yields and exclusively excellent enantioselectivities. The reaction is proposed to proceed according to a modified Houk-List model, in which the carboxylate moiety of the proline forms an assembly with the thiourea, enhancing the reactivity and selectivity of the catalyst. Moreover, the thiourea acts as a nonpolar counterpart to proline, circumventing its solubility limits in unpolar solvents such as hexane or toluene.