Diastereoisomeric Molecular Knots by Combination of Central and Topological Chiralities

We report an unprecedented example of diastereoisomerism created by reaction of topologically chiral molecular knots (knotanes) bearing hydroxy groups with centrochiral (1S)‐(+)‐camphor‐10‐sulfonyl chloride. The diastereoisomers of knotanes bearing on their periphery one and three camphorsulfonyl un...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-03, Vol.2004 (6), p.1236-1238
Main Authors: Lukin, Oleg, Yoneva, Albena, Vögtle, Fritz
Format: Article
Language:English
Subjects:
Chiral resolution
Chirality
Diastereoisomerism
Molecular knots
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Summary:We report an unprecedented example of diastereoisomerism created by reaction of topologically chiral molecular knots (knotanes) bearing hydroxy groups with centrochiral (1S)‐(+)‐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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300743