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Updated: Mar 9, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reactions: A Joint Experimental and Predictive
Eider Aranzamendi1, Sonia Arrasate1, Nuria Sotomayor1
1Departamento de Química Orgánica II Facultad de Ciencia y Tecnología Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU) Apdo. 644 48080 Bilbao Spain.
Abstract:
Enamides with a free NH group have been evaluated as nucleophiles in chiral Brønsted acid-catalyzed enantioselective α-amidoalkylation reactions of bicyclic hydroxylactams for the generation of quaternary stereocenters. A quantitative structure-reactivity relationship (QSRR) method has been developed to find a useful tool to rationalize the enantioselectivity in this and related processes and to orient the catalyst choice. This correlative perturbation theory (PT)-QSRR approach has been used to predict the effect of the structure of the substrate, nucleophile, and catalyst, as well as the experimental conditions, on the enantioselectivity. In this way, trends to improve the experimental results could be found without engaging in a long-term empirical investigation.
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