Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

作者：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

来源：Organic Letters, 2006, 8(23): 5369-5372.

DOI：10.1021/ol062204b

[GRAPHICS]
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.

• 出版日期2006-11-9