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Review

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

by
Jerzy Lisowski
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, Poland
Molecules 2022, 27(13), 4097; https://doi.org/10.3390/molecules27134097
Submission received: 31 May 2022 / Revised: 22 June 2022 / Accepted: 23 June 2022 / Published: 25 June 2022
(This article belongs to the Special Issue Design and Synthesis of Macrocyclic Compounds)
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Abstract

The condensation of aromatic dialdehydes with chiral diamines, such as 1,2-trans-diaminocyclohexane, leads to various enantiopure or meso-type macrocyclic Schiff bases, including [2 + 2], [3 + 3], [4 + 4], [6 + 6] and [8 + 8] condensation products. Unlike most cases of macrocycle synthesis, the [3 + 3] macrocycles of this type are sometimes obtained in high yields by direct condensation without a metal template. Macrocycles of other sizes from this family can often be selectively obtained in high yields by a suitable choice of metal template, solvent, or chirality of the building blocks. In particular, the application of a cadmium(II) template results in the expansion of the [2 + 2] macrocycles into giant [6 + 6] and [8 + 8] macrocycles. These imine macrocycles can be reduced to the corresponding macrocyclic amines which can act as hosts for the binding of multiple cations or multiple anions.
Keywords: macrocycles; chirality; imines; amines; metal binding; enantiomeric recognition macrocycles; chirality; imines; amines; metal binding; enantiomeric recognition
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MDPI and ACS Style

Lisowski, J. Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes. Molecules 2022, 27, 4097. https://doi.org/10.3390/molecules27134097

AMA Style

Lisowski J. Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes. Molecules. 2022; 27(13):4097. https://doi.org/10.3390/molecules27134097

Chicago/Turabian Style

Lisowski, Jerzy. 2022. "Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes" Molecules 27, no. 13: 4097. https://doi.org/10.3390/molecules27134097

APA Style

Lisowski, J. (2022). Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes. Molecules, 27(13), 4097. https://doi.org/10.3390/molecules27134097

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