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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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Article information


Submitted
22 Sep 2004
Accepted
30 Nov 2004
First published
10 Jan 2005

Org. Biomol. Chem., 2005,3, 524-537
Article type
Paper

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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