Dutch Resolution of a configurationally stable [5]helquat

作者：Severa Lukas^*; Sazelova Petra; Cisarova Ivana; Saman David; Koval Dusan; Devadig Pradeep; Kasicka Vaclav; Teply Filip^*

来源：Chirality, 2018, 30(3): 254-260.

DOI：10.1002/chir.22789

• anion exchange
• chiral capillary electrophoresis
• chirality assignment
• helical conformation
• racemization barrier
• single enantiomers
• tartrate anions family

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.

• 出版日期2018-3