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Jimeno, Ciril
Molecules (Basel, Switzerland), 02/2021, Letnik: 26, Številka: 4Journal Article
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 diastereomer in high ee. In contrast, the proline derivative yielded the diasteromer. MMFF models suggest the presence of an extensive hydrogen bonding network between the acylguanidinium group and the reaction intermediates.
