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Phenylseleny bromide-induced cyclisation of γ- and δ-unsaturated aldoxime and ketoxime O-allyl and O-benzyl ethers is followed by a slow fragmentation of the resultant oxyiminium ions furnishing cyclic iminium salts which are readily reduced to pyrrolidines, piperidines or tetrahydroisoquinolines by sodium borohydride; dialkenyl oximes yield indolizidines and quinolizidines by an analogous sequence...
Electrophile induced cyclisation of oximes onto endocyclic alkenes and exo-methylene cycloalkanes occurs stereo- and regio-specifically generating cis-fused bicyclic nitrones in good yield. Subsequent facially selective cycloaddition with N-methylmaleimide occurs in good yield. The sequence may be carried out as a one-pot procedure and results in the formation of 4 bonds, 2 rings and 6 stereocentres.
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