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New Macrocycles with Planar Chirality—Synthesis and Determination of Absolute Configurations
Author(s) -
Kalisiak Jarosław,
Skowronek Paweł,
Gawroński Jacek,
Jurczak Janusz
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501409
Subject(s) - chirality (physics) , planar , circular dichroism , planar chirality , absolute configuration , spectroscopy , dilution , crystallography , chemistry , correctness , materials science , stereochemistry , enantioselective synthesis , organic chemistry , mathematics , computer science , physics , algorithm , catalysis , chiral symmetry , thermodynamics , computer graphics (images) , quantum mechanics , nambu–jona lasinio model , quark
A versatile system for preparing macrocyclic compounds with planar chirality is presented. In this system chiral diazacoronands are synthesized readily from lariat‐type diesters 13 and 14 and unsymmetrical diamines 7, 8, 12, 15 , and 16 under non‐high‐dilution conditions. The title compounds were subjected to structural analysis by X‐ray crystallography and circular dichroism spectroscopy, and absolute configurations for two representative examples (compounds 2 and 3 ) were assigned by molecular modeling. The correctness of the theoretical approach was verified by the crystallographic results obtained experimentally.