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Amide-derived enols in enol-Ugi reactions: expanding horizons for peptidomimetic scaffold synthesis
José Luis Ramiro1, Ana G Neo1, Carlos F Marcos1
1Laboratory of Bioorganic Chemistry & Membrane Biophysics (L.O.B.O.). Departamento de Química Orgánica e Inorgánica. Universidad de Extremadura, 10003 Cáceres, Spain. cfernan@unex.es.
Abstract:
A highly efficient enol-Ugi reaction of β,β-diketoamides has been developed using a novel non-heterocyclic amide-stabilised enol. This approach enables a broad reaction scope, affording β-enaminoamide peptidomimetics with constrained conformations due to CH-π interaction and C(sp3)H⋯O hydrogen bonding. Notably, the use of a five-membered cyclic enol is crucial for achieving stable products in excellent yields. This work highlights the potential of the enol-Ugi reaction for constructing diverse peptidomimetic scaffolds.
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