Stereoselective formation of fused tricyclic amines from acyclic aldehydes by a cascade process involving condensation, cyclization, and dipolar cycloaddition.

@article{Burrell2009StereoselectiveFO,
  title={Stereoselective formation of fused tricyclic amines from acyclic aldehydes by a cascade process involving condensation, cyclization, and dipolar cycloaddition.},
  author={Adam J M Burrell and Iain Coldham and Luke Watson and Niall Oram and Christopher D Pilgram and Nathaniel G. Martin},
  journal={The Journal of organic chemistry},
  year={2009},
  volume={74 6},
  pages={2290-300}
}
The preparation of tricyclic amines from acyclic precursors is described using a cascade of tandem reactions involving condensation of an aldehyde with a primary amine, cyclization (with displacement of a halide), and then in situ deprotonation or decarboxylation to give an azomethine ylide or nitrone followed by intramolecular dipolar cycloaddition. The methodology is straightforward, and the aldehyde precursors are prepared easily and quickly in high yield using nitrile alkylations followed… CONTINUE READING