• Chemistry, Medicine
  • Published in
    Organic & biomolecular…
  • DOI:10.1039/B414747M

The synthesis and conformation of oxygenated trianglimine macrocycles.

  title={The synthesis and conformation of oxygenated trianglimine macrocycles.},
  author={Nikolai Kuhnert and Ana M L{\'o}pez-Periago and Giulia M. Rossignolo},
  journal={Organic & biomolecular chemistry},
  volume={3 3},
The synthesis of series of D(2h) and C(2v) symmetric oxygenated aromatic dicarboxaldehydes, using dilithiation methodology, is described along with their reactivity in the [3+3] cyclocondensation reaction with (1R,2R)-diaminocyclohexane to give oxygenated trianglimine macrocycles. Macrocycles derived from C(2v) symmetric dialdehydes give macrocycles with a stereogenic aromatic plane with complete diastereocontrol, as a mixture of rotamers.