Organic & Biomolecular Chemistry 2005-05-21

Tuning the size of macrocyclic cavities in trianglimine macrocycles.

Nikolai Kuhnert, Nicolai Burzlaff, Chirag Patel, Ana Lopez-Periago

Index: Org. Biomol. Chem. 3(10) , 1911-21, (2005)

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Abstract

The synthesis of aromatic dicarboxaldehydes is described along with their reactivity in the [3 + 3] cyclocondensation reaction with (1R,2R)-diaminocyclohexane to give trianglimine macrocycles. In particular, the scope and limitation of the reaction with regard to complete control of the cavity size of the macrocycles is discussed producing a total of 11 macrocycles with different cavity sizes ranging from 9 to 23 angstroms.