Lewis acid-mediated nucleophilic alkylations on chiral [6,3a,4]oxadiazaindano[5,4-a]isoquinolines. Asymmetric synthesis of 1-alkyl substituted tetrahydroisoquinolines

Article abstract of DOI:10.1016/0040-4039(96)01337-8

Lewis acid-mediated nucleophilic alkylation of the chiral [6,3a,4]oxadiazaindano[5,4-a]isoquinoline derivatives with various organometallic reagents leads to highly enantioselective synthesis of 1-alkyl substituted tetrahydroisoquinolines. This methodology was applied to the asymmetric synthesis of (-)-salsolidine and (+)-O-methylarmepavine.