Synthesis of Benzomorphan Analogues by Intramolecular Buchwald–Hartwig Cyclization

  title={Synthesis of Benzomorphan Analogues by Intramolecular Buchwald–Hartwig Cyclization},
  author={Anton S. Khartulyari and Martin E. Maier},
  journal={European Journal of Organic Chemistry},
A new strategy toward the important class of benzomorphans is described. The key bond formation is based on an intramolecular Buchwald–Hartwig enolate arylation reaction. Thus, alkylation of piperidones with ortho-bromobenzyl bromides provides the necessary substrates. In the presence of a palladium catalyst, a sterically hindered phosphane ligand, and a base, carbon–carbon bond formation to tricyclic benzomorphan derivatives takes place. After removal of the N-protecting group, derivatization… 
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