About: Preferential Crystallization of a Helicene-Viologen Hybrid - An Efficient Method to Resolve [5]Helquat Enantiomers on a 20 g Scale     Goto   Sponge   NotDistinct   Permalink

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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.
  • 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. (en)
Title
  • Preferential Crystallization of a Helicene-Viologen Hybrid - An Efficient Method to Resolve [5]Helquat Enantiomers on a 20 g Scale
  • Preferential Crystallization of a Helicene-Viologen Hybrid - An Efficient Method to Resolve [5]Helquat Enantiomers on a 20 g Scale (en)
skos:prefLabel
  • Preferential Crystallization of a Helicene-Viologen Hybrid - An Efficient Method to Resolve [5]Helquat Enantiomers on a 20 g Scale
  • Preferential Crystallization of a Helicene-Viologen Hybrid - An Efficient Method to Resolve [5]Helquat Enantiomers on a 20 g Scale (en)
skos:notation
  • RIV/61388963:_____/12:00379101!RIV13-AV0-61388963
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(GA203/08/1428), P(GAP207/10/2391), P(GP203/09/P485), Z(AV0Z40550506), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika
  • 3
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
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http://linked.open...dnocenehoVysledku
  • 161199
http://linked.open...ai/riv/idVysledku
  • RIV/61388963:_____/12:00379101
http://linked.open...riv/jazykVysledku
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  • helical structures; helicene-viologen hybrid; crystal growth; synthetic methods; conglomerates (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [BA75C2133307]
http://linked.open...i/riv/nazevZdroje
  • European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor
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http://linked.open...vavai/riv/projekt
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http://linked.open...iv/tvurceVysledku
  • Císařová, I.
  • Kašička, Václav
  • Koval, Dušan
  • Severa, Lukáš
  • Teplý, Filip
  • Vávra, Jan
  • Švec, Pavel
  • Sázelová, Petra
http://linked.open...ain/vavai/riv/wos
  • 000299295700008
http://linked.open...n/vavai/riv/zamer
issn
  • 1434-193X
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/ejoc.201101367
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