The development of synthetic methods that utilize simple and stable precursors as well as multicomponent reactions, which lead to the formation of two or more C-C/C-N bonds, in a one-pot process, is of great appeal to the synthesis community. The amide motif constitutes the core of several natural products (e.g., penicillin), biopolymers (e.g., proteins and nylon), ligands, fragrances, pharmaceuticals and agrochemicals. Additionally, it embodies a class of powerful activating/directing and protecting groups that facilitate C-C and C-N bond forming events. In this study, a one-pot protocol for N-alkylation, ester-ketonation and chemoselective C-enolate trapping of readily affordable γ-amido esters is described. The functionalized products are subsequently elaborated to some medicinally important architectures, including vinylogous lactams and N-heterocyclic 1,3-diynes.

One-pot N-alkylation, ketonation and C-enolate alkylation of readily affordable γ-amido esters: Application to the synthesis of functionalized lactams

253rd National Meeting (2017)

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