A synthetic protocol for the preparation of α-acyl
aminocarboxamides
and α-amino amidines is proposed. The selectivity toward each
of these two possible products was tuned by simple modifications of
the reaction conditions. A broad scope is presented, allowing access
to the desired products in up to 87% (Ugi adduct) and 93% (α-amino
amidine). Theoretical calculations were carried out, and the analysis
led to the proposal of a new mechanistic pathway for the Ugi reaction,
in which methanol acts not only as the solvent but also as a reagent.
High-resolution (tandem) mass spectrometry experiments allowed the
detection and characterization of the key intermediate associated
with this new and alternative reaction pathway, thus supporting the
theoretical proposal.
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