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Issue 6, 2010
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Resolution of a configurationally stable [5]helquat: enantiocomposition analysis of a helicene congener by capillary electrophoresis

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Abstract

Racemic [5]helquat as a triflate salt has been synthesized using a robust, three-step procedure. Subsequent exchange of triflate anions for inexpensive (R,R)-dibenzoyltartrate anions via an ion exchange resin afforded two diastereoisomeric salts. Crystallization led to the resolution of the helquat (ee > 98%). This is the first time that a non-racemic helquat has been obtained; its helicity having been assigned and its racemization barrier determined. Capillary electrophoresis with a sulfated β-cyclodextrin chiral selector is introduced for the first time as a straightforward method to analyze the enantiocomposition of charged, helicene-like species.

Graphical abstract: Resolution of a configurationally stable [5]helquat: enantiocomposition analysis of a helicene congener by capillary electrophoresis

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Article information


Submitted
01 Feb 2010
Accepted
26 Feb 2010
First published
18 Mar 2010

New J. Chem., 2010,34, 1063-1067
Article type
Letter

Resolution of a configurationally stable [5]helquat: enantiocomposition analysis of a helicene congener by capillary electrophoresis

L. Severa, D. Koval, P. Novotná, M. Ončák, P. Sázelová, D. Šaman, P. Slavíček, M. Urbanová, V. Kašička and F. Teplý, New J. Chem., 2010, 34, 1063
DOI: 10.1039/C0NJ00085J

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