Cycloadditions of nonstabilized 2-azaallyllithiums with cycloheptatriene.
[reaction: see text] Transmetalation of tin-bearing cyclic imidates gave 2-azaallyllithiums that underwent [pi6s + pi4s] cycloadditions with cycloheptatriene to produce tricyclic adducts, which may be useful as analogs of cocaine. The peri- and stereoselectivity of this process are discussed.
Department of Chemistry, University of Michigan, Ann Arbor 48109-1055, USA. wpearson@umich.edu
William H
WH
Pearson
Douglas M
DM
Mans
Jeff W
JW
Kampf
D001372:Aza Compounds / Q000737:chemistry; D003042:Cocaine / Q000031:analogs & derivatives*; D003508:Cycloheptanes / Q000737:chemistry; D004583:Electrons; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis*; D018020:Lithium Compounds / Q000737:chemistry; D011090:Polyenes
D001372:Aza Compounds; D003508:Cycloheptanes; D006572:Heterocyclic Compounds, Bridged-Ring; D018020:Lithium Compounds; D011090:Polyenes; D003042:Cocaine