Synthesis of Octahydroquinolines through the Lewis Acid Catalyzed Reaction of Vinyl Allenes and Imines

The reaction of vinyl allenes with imines under Lewis acid catalysis has been explored. Vinyl allenes
in which the allenic portion of the molecule is tri- or tetrasubstituted gave octahydroquinoline
derivatives as single isomers together with a minor compound formed by an ene reaction of the
imine with the allene. Compounds in which the allene is 1,3-disubstituted do not react under the
conditions assayed.