Synfacts 2009(2): 0217-0217  
DOI: 10.1055/s-0028-1087587
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Biomimetic Chemoselectivity Control of Aldol Reactions

Contributor(s): Benjamin List, Lars Ratjen
Y. Chi, S. T. Scroggins, E. Boz, J. M. J. Fréchet*
University of California, Berkeley, USA
Further Information

Publication History

Publication Date:
22 January 2009 (online)


The synthesis and utilization of polymeric catalyst 1 bearing proline moieties as active sites is reported. This catalyst aggregate was applied successfully in aldol reactions of aldehydes and ketones in aqueous media. In a self-­aldol process of butanal, mainly reversibly formed β-hydroxyaldehyde 2 was obtained, whereas the formation of aldol condensation product 3 could be suppressed. These results were transferred to more complex dynamic catalytic cross-aldol reactions, giving rise to α,β-unsaturated ketones 4, favored over formation of self-condensation product 5. The likewise expected ketones 6 were not observed.