Influence of Non-Covalent Interactions in the Exo- and Regioselectivity of Aza-Diels-Alder Reactions: Experimental and DFT Calculations

Gallardo-Fuentes, Sebastian; Lezana, Nicolas; Luhr, Susan; Galdamez, Antonio; Vilches-Herrera, Marcelo

Abstract

A systematic experimental and theoretical study of the intermolecular Aza-Diels-Alder reaction using 5-aminopyrrole as a building block shows that the commonly accepted endo selectivity, ruled by controversial secondary orbital interactions, are overcome by non-covalent interactions affording to the unusual exo adduct. Additionally, the regioselectivity is also influenced for such interactions. The starting materials are easily prepared, and the use of water as the solvent is a great achievement for the development of cleaner synthetic methodologies.

Más información

Título según WOS: Influence of Non-Covalent Interactions in the Exo- and Regioselectivity of Aza-Diels-Alder Reactions: Experimental and DFT Calculations
Título según SCOPUS: Influence of non-covalent interactions in the exo- A nd regioselectivity of aza-diels-alder reactions: Experimental and DFT calculations
Título de la Revista: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 84
Número: 17
Editorial: AMER CHEMICAL SOC
Fecha de publicación: 2019
Página de inicio: 10825
Página final: 10831
Idioma: English
DOI:

10.1021/acs.joc.9b01390

Notas: ISI, SCOPUS