Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 17, Pages 10825-10831Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01390
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Funding
- CONICYT project FONDECYT Initiation [11160465]
- FONDECYT [3170653]
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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.
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