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Improved Stereochemical Analysis of Conformationally Flexible Diamines by Binding to a Bisporphyrin Molecular Clip
Author(s) -
Norrehed Sara,
Johansson Henrik,
Grennberg Helena,
Gogoll Adolf
Publication year - 2013
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.201300533
Subject(s) - stereocenter , chemistry , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , catalysis , enantioselective synthesis
The relative stereochemistry of acyclic diamines with several stereogenic centers has been analyzed by NMR spectroscopy in combination with conformational deconvolution. Binding to a bisporphyrin molecular clip improves the stereochemical assignment significantly. The diamines were synthesized from inexpensive sugar alcohols, and their stable hydrochlorides were quantitatively converted into free bases by treatment with ion‐exchange resin.