jo9b01390_si_002.cif (15.3 kB)
Influence of Non-Covalent Interactions in the Exo- and Regioselectivity of Aza-Diels–Alder Reactions: Experimental and DFT Calculations
dataset
posted on 2019-08-23, 22:43 authored by Sebastián Gallardo-Fuentes, Nicolás Lezana, Susan Lühr, Antonio Galdámez, Marcelo Vilches-HerreraA 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.