Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

M. Paravidino, R.S. Bon, R. Scheffelaar, D.J. Vugts, A. Znabet, R.F. Schmitz, F.J.J. de Kanter, M. Lutz, A.L Spek, M.B. Groen, R.V.A. Orru

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

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. © 2006 American Chemical Society.
Original languageEnglish
Pages (from-to)5369-72
JournalOrganic letters
Volume8
Issue number23
DOIs
Publication statusPublished - 2006

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