Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction

The binding and stabilizing effect of arginine residues in certain aldolases served as inspiring source for the development of a family of amino acylguanidine organocatalysts. Screening and optimization led to identify the threonine derivative as the most suitable catalyst for the asymmetric aldol addition of hydroxyacetone, affording the syn diastereomer in high ee. In contrast, the proline derivative yielded the anti diasteromer. MMFF models suggest the presence of an extensive hydrogen bonding network between the acylguanidinium group and the reaction intermediates.

Automated summary

The research was inspired by the binding and stabilizing effect of arginine residues in certain aldolases, leading to the development of a new family of amino acylguanidine organocatalysts. Screening and optimization identified the threonine derivative as the most suitable catalyst for asymmetric aldol addition, while the proline derivative yielded the anti diastereomer. MMFF models indicated the presence of an extensive hydrogen bonding network between the acylguanidinium group and the reaction intermediates.