Stereoselective Desymmetrizations of Dinitriles to Synthesize Lactones

Tetrahedron Lett. 2022 Jan 5:88:153573. doi: 10.1016/j.tetlet.2021.153573. Epub 2021 Dec 3.

Abstract

Nitriles are important organic functional groups, allowing for installation of nitrogen in organic synthesis. The Pinner reaction transforms nitriles into esters via the imidate group, but in general has previously necessitated harsh acid conditions. This work builds on the utility of the Pinner reaction through a stereoselective desymmetrization of dinitriles to form γ- and δ-lactones in good yields and diastereoselectivites.

Keywords: Desymmetrization; Diastereoselective; Lactones; Pinner Reaction.