N-heterocyclic carbene catalysis as a tool for gaining access to the 3,4-dihydropyran-2-one skeleton
Articolo
Data di Pubblicazione:
2014
Citazione:
N-heterocyclic carbene catalysis as a tool for gaining access to the 3,4-dihydropyran-2-one skeleton / D. Albanese, N. Gaggero. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 26(2014), pp. 5631-5640. [10.1002/ejoc.201402024]
Abstract:
An overview of the progress made in the synthesis of 3,4-dihydropyran-2-ones since the development of NHC catalysis is reported. Two distinct classes of species - electrophilic alpha,beta-unsaturated acylazolium and nucleophilic azolium enol/enolate intermediates - can easily be produced from different substrates through the intermediacy of NHC catalysis. They enable the construction of the 3,4-dihydropyran-2-one skeleton, the core of natural and synthetic products with significant biological activities, through Michael additions, cycloadditions and rearrangements.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
3,4-Dihydropyran-2-ones; Michael addition; N-Heterocyclic carbenes; alpha,beta-Unsaturated acyl azolium ions; Azolium enols; Azolium enolates; Oxygen heterocycles
Elenco autori:
D. Albanese, N. Gaggero
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