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

0345961 - ÚOCHB 2011 RIV GB eng J - Článek v odborném periodiku
Severa, Lukáš - Koval, Dušan - Novotná, P. - Ončák, M. - Sázelová, Petra - Šaman, David - Slavíček, P. - Urbanová, M. - Kašička, Václav - Teplý, Filip
Resolution of a configurationally stable [5]helquat. enantiocomposition analysis of a helicene congener by capillary electrophoresis.
New Journal of Chemistry. Roč. 34, č. 6 (2010), s. 1063-1067. ISSN 1144-0546. E-ISSN 1369-9261
Grant CEP: GA ČR GA203/09/1614; GA ČR GA203/09/0705; GA ČR(CZ) GA203/08/1428; GA ČR GAP207/10/2391
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: [5]helquat * capillary electrophoresis * resolution via diastereoisomers
Kód oboru RIV: CF - Fyzikální chemie a teoretická chemie
Impakt faktor: 2.631, rok: 2010

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.
Trvalý link: http://hdl.handle.net/11104/0187117