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

Autor:	Nicolás Lezana, Sebastián Gallardo-Fuentes, Susan Lühr, Marcelo Vilches-Herrera, Antonio Galdámez
Rok vydání:	2019
Předmět:	chemistry.chemical_classification 010405 organic chemistry Chemistry Organic Chemistry Intermolecular force Regioselectivity 010402 general chemistry 01 natural sciences 0104 chemical sciences Adduct Solvent Computational chemistry Diels alder Non-covalent interactions Selectivity
Zdroj:	The Journal of Organic Chemistry. 84:10825-10831
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.9b01390
Popis:	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.
Databáze:	OpenAIRE
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