Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes
James E. McGettigan, Joseph M. Ready
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.
Topics & Concepts
ChemistryAlkylationRacemizationCombinatorial chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistryAsymmetric Synthesis and Catalysis