Asymmetric synthesis of substituted tropinones using the intramolecular mannich cyclization reaction and acyclic N-sulfinyl beta-amino ketone ketals.
Sulfinimine-derived, enantiopure N-sulfinyl beta-amino ketone ketals on hydrolysis give dehydropyrrolidine ketones that on treatment with (Boc)(2)O/DMAP afford substituted tropinones in good yield.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
Theddu
Naresh
N
Gaspari
Paul M
PM
D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
D007097:Imines; D007659:Ketones; D013452:Sulfonium Compounds; D014326:Tropanes; C522016:sulfinimine; C016808:3-tropinone