Asymmetric synthesis of 1-substituted tetrahydroisoquinolines by nucleophilic addition to hydrazonium ions. Application to the enantioselective syntheses of (+)- and (-)-salsolidines and (-)-cryptostyline II

Article abstract of DOI:10.1016/00404-0399(50)1358-O

Nucleophilic addition of carbon nucleophiles and metal hydride reagents to hydrazonium salts modified by optically active 2-substituted pyrrolidine auxiliaries leads to highly enantioselective synthesis of 1-substituted tetrahydroisoquinolines. This methodology was applied to asymmetric synthesis of the title isoquinoline alkaloids.