Diastereoselective Multicomponent Synthesis of Dihydropyridones with an Isocyanide Functionality

In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this...

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Bibliographic Details
Published in:Organic letters 2006-11, Vol.8 (23), p.5369-5372
Main Authors: Paravidino, Monica, Bon, Robin S, Scheffelaar, Rachel, Vugts, Danielle J, Znabet, Anass, Schmitz, Rob F, de Kanter, Frans J. J, Lutz, Martin, Spek, Anthony L, Groen, Marinus B, Orru, Romano V. A
Format: Article
Language:English
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Summary:In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062204b