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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzaldehydes / chemical synthesis
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Benzaldehydes / chemistry
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Cyclization
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / chemistry
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Macrocyclic Compounds / chemical synthesis*
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Macrocyclic Compounds / chemistry
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Magnetic Resonance Spectroscopy
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Molecular Conformation
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Oxygen / chemistry*
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Sensitivity and Specificity
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Stereoisomerism
Substances
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Benzaldehydes
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Heterocyclic Compounds
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Macrocyclic Compounds
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trianglimine
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Oxygen