Lewis acid-mediated diastereoselective hydrocyanation of enamides

Abstract

Enamides are versatile synthetic blocks used as the starting materials for accessing a diverse range of organic compounds with potential biological activity. Currently, there are many examples of functionalization of enamides through the electrophilic addition mechanism, which are primarily catalyzed by transition metals and phosphoric acids. These efficient and selective transformations allow the synthesis of a diverse range of organic compounds, such as chiral amines, sulfonylamides, and chromanols. However, despite the abundance of literature sources on the addition to enamides, there is an apparent lack of reports describing the hydrocyanation reaction of enamides, especially in the context of N-heterocyclic tertiary enamides, thus underlying the current gap in assessing N-heterocyclic nitriles from enamides. Thus, the following thesis aims to develop and optimize an efficient, stereoselective, and cost-effective procedure of hydrocyanation of enamides mediated by BF3·Et2O and H2O. Furthermore, the thesis aims to explore the substrate scope of enamides and propose diversification strategies for further synthesis of organic compounds from the resulting nitriles.