Influence of Non-Covalent
Interactions in the Exo- and Regioselectivity of
Aza-Diels–Alder Reactions:
Experimental and DFT Calculations
Posted on 2019-08-23 - 22:43
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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Gallardo-Fuentes, Sebastián; Lezana, Nicolás; Lühr, Susan; Galdámez, Antonio; Vilches-Herrera, Marcelo (2019). Influence of Non-Covalent
Interactions in the Exo- and Regioselectivity of
Aza-Diels–Alder Reactions:
Experimental and DFT Calculations. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.9b01390
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AUTHORS (5)
SG
Sebastián Gallardo-Fuentes
NL
Nicolás Lezana
SL
Susan Lühr
AG
Antonio Galdámez
MV
Marcelo Vilches-Herrera