Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes

Angew Chem Int Ed Engl. 2023 Apr 11;62(16):e202216961. doi: 10.1002/anie.202216961. Epub 2023 Mar 6.

Abstract

Alkenyl boronate complexes react with acylated quinolines and isoquinolines via 1,2-metalate rearrangement to give alkylated, dearomatized heterocycles in good yields, diastereoselectivities, and regioselectivities. This multi-component coupling is highly modular and can be used to access a wide scope of heterocyclic scaffolds. Chiral boronic esters made through this methodology possess high synthetic potential and can be transformed into various functional groups in one step without racemization.

Keywords: Alkenyl Boronate; Isoquinolines; Multicomponent Coupling; Quinolines.