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.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Pack
Shawn K
SK
D000478:Alkylation; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D028581:Lanthanoid Series Elements / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D006571:Heterocyclic Compounds; D007212:Indolizines; D028581:Lanthanoid Series Elements; D009942:Organometallic Compounds; D011759:Pyrrolidines; D011807:Quinolizines