Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

Monica Paravidino, Robin S. Bon, Rachel Scheffelaar, Danielle J. Vugts, Anass Znabet, Rob F. Schmitz, Frans J.J. De Kanter, Martin Lutz, Anthony L. Spek, Marinus B. Groen, Romano V.A. Orru*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review


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.

Original languageEnglish
Pages (from-to)5369-5372
Number of pages4
JournalOrganic Letters
Issue number23
Publication statusPublished - 9 Nov 2006
Externally publishedYes

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