Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes.

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.