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Preferential Crystallization of a Helicene-Viologen Hybrid - An Efficient Method to Resolve [5]Helquat Enantiomers on a 20 g Scale
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SYSNO ASEP 0379101 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Preferential Crystallization of a Helicene-Viologen Hybrid - An Efficient Method to Resolve [5]Helquat Enantiomers on a 20 g Scale Author(s) Vávra, Jan (UOCHB-X) RID
Severa, Lukáš (UOCHB-X) RID, ORCID
Švec, Pavel (UOCHB-X) ORCID, RID
Císařová, I. (CZ)
Koval, Dušan (UOCHB-X) RID, ORCID
Sázelová, Petra (UOCHB-X) RID, ORCID
Kašička, Václav (UOCHB-X) RID, ORCID
Teplý, Filip (UOCHB-X) RID, ORCIDNumber of authors 8 Source Title European Journal of Organic Chemistry - ISSN 1434-193X
-, č. 3 (2012), s. 489-499Number of pages 11 s. Language eng - English Country DE - Germany Keywords helical structures ; helicene-viologen hybrid ; crystal growth ; synthetic methods ; conglomerates Subject RIV CC - Organic Chemistry R&D Projects GAP207/10/2391 GA ČR - Czech Science Foundation (CSF) GA203/08/1428 GA ČR - Czech Science Foundation (CSF) GP203/09/P485 GA ČR - Czech Science Foundation (CSF) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000299295700008 DOI https://doi.org/10.1002/ejoc.201101367 Annotation The bistriflate salt of racemic [5]helquat 1 was found to form a conglomerate. Based on this finding, the preferential crystallization of this chiral helicene–viologen hybrid was developed to deliver pure enantiomers on a 20 g scale (10.5 g of each enantiomer). To the best of our knowledge, this is the largest amount of nonracemic helicene-like compound obtained by preferential crystallization to date. The absolute configuration of the P enantiomer was confirmed by X-ray crystal structure analysis. The chromatography-free synthesis of racemic 1 on a multigram scale (30 g) is also presented as an entry point to this resolution study. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2013
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