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Issue 3, 2005
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The synthesis and conformation of oxygenated trianglimine macrocycles

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Abstract

The synthesis of series of D2h and C2v 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 C2v symmetric dialdehydes give macrocycles with a stereogenic aromatic plane with complete diastereocontrol, as a mixture of rotamers.

Graphical abstract: The synthesis and conformation of oxygenated trianglimine macrocycles

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Publication details

The article was received on 22 Sep 2004, accepted on 30 Nov 2004 and first published on 10 Jan 2005


Article type: Paper
DOI: 10.1039/B414747M
Citation: Org. Biomol. Chem., 2005,3, 524-537
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    The synthesis and conformation of oxygenated trianglimine macrocycles

    N. Kuhnert, A. Lopez-Periago and G. M. Rossignolo, Org. Biomol. Chem., 2005, 3, 524
    DOI: 10.1039/B414747M

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