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Intramolecular Versus Intermolecular Induction of Helical Handedness in Pyridinedicarboxamide Oligomers
Author(s) -
Maurizot Victor,
Dolain Christel,
Huc Ivan
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400641
Subject(s) - intramolecular force , chemistry , intermolecular force , oligomer , asymmetric induction , circular dichroism , stereochemistry , polymer chemistry , molecule , organic chemistry , enantioselective synthesis , catalysis
A new convergent synthetic scheme has been developed to prepare oligoamides of 2,6‐diaminopyridine and 4‐decyloxy‐2,6‐pyridinedicarboxylic acid. These compounds adopt stable single helical conformations in solution. NMR and circular dichroism studies show that intramolecular and intermolecular chiral induction of handedness in these helices is possible. Intramolecular induction is effected by attaching a single chiral group to the end of an oligomer. Intermolecular induction results from various noncovalent interactions between chiral carboxylic or sulfonic acids and the terminal residues of the oligoamides. Intramolecular induction appears to be more efficient than intermolecular induction. When both effects compete, intramolecular induction prevails. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)