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

SYSNO ASEP	0345961
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Resolution of a configurationally stable [5]helquat. enantiocomposition analysis of a helicene congener by capillary electrophoresis
Author(s)	Severa, Lukáš (UOCHB-X)_{RID, ORCID} Koval, Dušan (UOCHB-X)_{RID, ORCID} Novotná, P. (CZ) Ončák, M. (CZ) Sázelová, Petra (UOCHB-X)_{RID, ORCID} Šaman, David (UOCHB-X)_{RID, ORCID} Slavíček, P. (CZ) Urbanová, M. (CZ) Kašička, Václav (UOCHB-X)_{RID, ORCID} Teplý, Filip (UOCHB-X)_{RID, ORCID}
Number of authors	10
Source Title	New Journal of Chemistry. - : Royal Society of Chemistry - ISSN 1144-0546 Roč. 34, č. 6 (2010), s. 1063-1067
Number of pages	5 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	[5]helquat ; capillary electrophoresis ; resolution via diastereoisomers
Subject RIV	CF - Physical ; Theoretical Chemistry
R&D Projects	GA203/09/1614 GA ČR - Czech Science Foundation (CSF)
	GA203/09/0705 GA ČR - Czech Science Foundation (CSF)
	GA203/08/1428 GA ČR - Czech Science Foundation (CSF)
	GAP207/10/2391 GA ČR - Czech Science Foundation (CSF)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000278275700004
DOI	10.1039/c0nj00085j
Annotation	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.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2011

Number of the records: 1