Determining the Scope of the Organolanthanide-Catalyzed, Sequential Intramolecular Amination/Cyclization Reaction: Formation of Substituted Quinolizidines, Indolizidines, and Pyrrolizidines

The scope of the lanthanide-mediated, intramolecular amination/cyclization reaction was determined
for the formation of substituted quinolizidines, indolizidines, and pyrrolizidines. A methyl group
was installed at diverse positions in the substrates to determine the sense and magnitude of
diastereoselection. High diastereoselectivity (>20:1) was achieved for the formation of some
quinolizidines and indolizidines. The sense of relative asymmetric induction was contrary to
previously studied systems, and although some questions remain, a rationalization for these results
is put forward.