title: The synthesis and conformation of oxygenated trianglimine macrocycles.
abstract: 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.
authors.affiliation: Supramolecular and Biomolecular Chemistry Laboratory, School of Biomedical and Molecular Sciences, The University of Surrey, Guildford GU2 7XH, UK. n.kuhnert@surrey.ac.uk
authors.forename: Nikolai
authors.initials: N
authors.lastname: Kuhnert
authors.forename: Ana
authors.initials: A
authors.lastname: Lopez-Periago
authors.forename: Giulia M
authors.initials: GM
authors.lastname: Rossignolo
mesh_terms: D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry*; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
chemical_list: D001547:Benzaldehydes; D006571:Heterocyclic Compounds; D047028:Macrocyclic Compounds; C511280:trianglimine; D010100:Oxygen