期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 26, 页码 5631-5640出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402024
关键词
3,4-Dihydropyran-2-ones; Michael addition; N-Heterocyclic carbenes; alpha,beta-Unsaturated acyl azolium ions; Azolium enols; Azolium enolates; Oxygen heterocycles
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.
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