Abstract
The formation of chiral non-racemic perazamacrocyles containing three or more nitrogen atoms in the form of identical of different functionalities can be achieved by diverse methodologies which usually exploit the sequential formation of carbon-nitrogen bonds by reaction of nucleophilic nitrogen functions with electrophilic compounds. The rigidity and restricted flexibility of the reaction partners is generally a requisite for the successful cyclization, which can be alternatively accomplished by the use of a metal template. The carbon stereocenters in the formed macrocycle are generally present in the starting nitrogen-containing reagent, e.g. amine, diamine, α- aminoacid and their derivatives. Intrinsically chiral porphyrins, lacking carbon stereocenters, have been also prepared. Chiral perazamacrocycles and their metal complexes have found applications in the fields of biomedical research, diagnosis, anion sensing, molecular recognition, enantiomeric discrimination, asymmetric catalysis, and material chemistry.
Keywords: Asymmetric catalysis, cyclization, enantioselective recognition, metal complexes, perazamacrocycles, porphyrins, supramolecular chemistry
Current Organic Synthesis
Title: Chiral Perazamacrocycles: Synthesis and Applications. Part 2
Volume: 6 Issue: 2
Author(s): D. Savoia and A. Gualandi
Affiliation:
Keywords: Asymmetric catalysis, cyclization, enantioselective recognition, metal complexes, perazamacrocycles, porphyrins, supramolecular chemistry
Abstract: The formation of chiral non-racemic perazamacrocyles containing three or more nitrogen atoms in the form of identical of different functionalities can be achieved by diverse methodologies which usually exploit the sequential formation of carbon-nitrogen bonds by reaction of nucleophilic nitrogen functions with electrophilic compounds. The rigidity and restricted flexibility of the reaction partners is generally a requisite for the successful cyclization, which can be alternatively accomplished by the use of a metal template. The carbon stereocenters in the formed macrocycle are generally present in the starting nitrogen-containing reagent, e.g. amine, diamine, α- aminoacid and their derivatives. Intrinsically chiral porphyrins, lacking carbon stereocenters, have been also prepared. Chiral perazamacrocycles and their metal complexes have found applications in the fields of biomedical research, diagnosis, anion sensing, molecular recognition, enantiomeric discrimination, asymmetric catalysis, and material chemistry.
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Cite this article as:
Savoia D. and Gualandi A., Chiral Perazamacrocycles: Synthesis and Applications. Part 2, Current Organic Synthesis 2009; 6 (2) . https://dx.doi.org/10.2174/157017909788167266
DOI https://dx.doi.org/10.2174/157017909788167266 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
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