Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reactions: A Joint Experimental and Predictive Study

Overview

Journal ChemistryOpen

Specialty Chemistry

Date 2016 Dec 30

PMID 28032023

Citations 7

Authors

Eider Aranzamendi

Sonia Arrasate

Nuria Sotomayor

Humberto Gonzalez-Diaz

Esther Lete

Affiliations

Soon will be listed here.

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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