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Diastereoisomeric Molecular Knots by Combination of Central and Topological Chiralities
Author(s) -
Lukin Oleg,
Yoneva Albena,
Vögtle Fritz
Publication year - 2004
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.200300743
Subject(s) - chemistry , diastereomer , camphor , silica gel , stereochemistry , chromatography , topology (electrical circuits) , organic chemistry , combinatorics , mathematics
We report an unprecedented example of diastereoisomerism created by reaction of topologically chiral molecular knots (knotanes) bearing hydroxy groups with centrochiral (1 S )‐(+)‐camphor‐10‐sulfonyl chloride. The diastereoisomers of knotanes bearing on their periphery one and three camphorsulfonyl units have been completely separated using commercial silica gel (Kromasil) and chiral (Chiralpak AD) HPLC columns respectively. The circular dichroisms of the separated samples have been measured and consequences of the chiral induction discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)