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Updated: Nov 18, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction
1Department of Biological Chemistry, Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Jordi Girona 18-26, E08034 Barcelona, Spain.
Abstract:
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.
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