Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 3, Pages 489-499Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101367
Keywords
Helical structures; Helicene-viologen hybrid; Chiral resolution; Conglomerates; Crystal growth; Synthetic methods
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Funding
- Czech Science Foundation [P207/10/2391, 203/08/1428, 203/09/P485]
- Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v. v. i. [Z4 055 0506]
- Ministry of Education, Youth and Sports of the Czech Republic [MSM0021620857]
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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.
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