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.

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]

N-heterocyclic carbene catalysis as a tool for gaining access to the 3,4-dihydropyran-2-one skeleton

D. Albanese
Primo
;
N. Gaggero
2014

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.
3,4-Dihydropyran-2-ones; Michael addition; N-Heterocyclic carbenes; alpha,beta-Unsaturated acyl azolium ions; Azolium enols; Azolium enolates; Oxygen heterocycles
Settore CHIM/06 - Chimica Organica
2014
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/238225
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