Nucleophilic Addition of Organometallic Reagents to Cinchona Alkaloids: Simple Access to Diverse Architectures

Abstract

Aminal pharm: Grignard reagents undergo a surprising nucleophilic aromatic addition reaction to cinchona alkaloids to stereoselectively produce cyclic aminals. Structurally diverse alkaloid derivatives with rigid cores that bear reactive functional groups (see examples) can be readily synthesized by this simple nucleophilic alkylation protocol.