Electroorganic Chemistry. 62. Reaction of Iminium Ion with Nuclophile: A Versatile Synthesis of Tetrahydroquinolines and Julolidines

Article abstract of DOI:10.1021/ja00385a033

A versatile synthetic method of tetrahydroquinolines and julolidines has been developed.The method involves the anodic oxidation of N,N-dimethylaniline in methanol to afford α-methoxylated or α,α'-dimethoxylated compounds and subsequent treatment of the products with Lewis acids in the presence of nucleophiles.Simple and electron-rich olefins such as alkenes, styrene, enol ethers, silyl enol ethers, enamines, and enol esters are usable as the nucleophiles.The intermediary formation of iminium ions from the methoxylated compounds is proposed as one of the key steps.The nucleophilic reaction od Grignard reagents with the methoxylated compounds in the presence of Lewis acid is also described.