Dutch Resolution of a configurationally stable [5]helquat

0489617 - ÚOCHB 2019 RIV US eng J - Článek v odborném periodiku
Severa, Lukáš - Sázelová, Petra - Císařová, I. - Šaman, David - Koval, Dušan - Devadig, Pradeep - Kašička, Václav - Teplý, Filip
Dutch Resolution of a configurationally stable [5]helquat.
Chirality. Roč. 30, č. 3 (2018), s. 254-260. ISSN 0899-0042. E-ISSN 1520-636X
Grant CEP: GA ČR(CZ) GA15-01948S; GA ČR(CZ) GA17-12648S; GA ČR(CZ) GA17-04393S
Institucionální podpora: RVO:61388963
Klíčová slova: anion exchange * chiral capillary electrophoresis * chirality assignment * helical conformation * racemization barrier * single enantiomers * tartrate anions family
Obor OECD: Organic chemistry
Impakt faktor: 1.927, rok: 2018

Synthesis and nontrivial optical resolution of a helicene-like dication, helquat 1, has been accomplished. Starting with gram scale of the racemic helquat 1 sample, Dutch Resolution using family of 3 tartrate anions was key to achieve successful separation of M and P helical enantiomers of 1. Hundreds of milligrams of each enantiomer of this configurationally stable C-2-symmetric helquat have been obtained. Racemization barrier of 1 has been determined. To our knowledge this is the first report on Dutch Resolution performed with a helicene-like compound. Moreover, there are no literature precedents for Dutch Resolution of chiral quaternary ammonium cations.
Trvalý link: http://hdl.handle.net/11104/0284000