Enantioselective Lewis base catalysed allylation of picoline- and quinaldine-based latent pronucleophiles

Abstract

Picolines and quinaldines are valuable building blocks and intermediates in the synthesis of natural products and pharmaceuticals. Functionalization of the methyl group in picolines and quinaldines under mild conditions is challenging. We report that the concept of latent pronucleophiles enables Lewis base catalysed allylation of picolines and quinaldines with allylic fluorides starting from silylated picolines and quinaldines. Reactions afford enantioenriched allylation products when chiral Lewis base catalysts are used. The allylation products can be rapidly transformed to quinolizine-4-ones.