The synthesis and conformation of oxygenated trianglimine macrocycles.
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.
Kuhnert
Nikolai
N
Supramolecular and Biomolecular Chemistry Laboratory, School of Biomedical and Molecular Sciences, The University of Surrey, Guildford GU2 7XH, UK. n.kuhnert@surrey.ac.uk
Lopez-Periago
Ana
A
Rossignolo
Giulia M
GM
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
D001547:Benzaldehydes; D006571:Heterocyclic Compounds; D047028:Macrocyclic Compounds; C511280:trianglimine; D010100:Oxygen