Dutch Resolution of a configurationally stable [5]helquat. Issue 3 (2nd January 2018)

• Record Type: Journal Article
• Authors: Severa, Lukáš; Sázelová, Petra; Císařová, Ivana; Šaman, David; Koval, Dušan; Devadig, Pradeep; Kašička, Václav; Teplý, Filip
• Is Part Of: Chirality. Volume 30:Issue 3(2018)
• Page Start: 254
• Page End: 260
• Publication Date: 2018-01-02
• Subjects: anion exchange -- chiral capillary electrophoresis -- chirality assignment -- helical conformation -- racemization barrier -- single enantiomers -- tartrate anions family; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22789
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: Synthesis and nontrivial optical resolution of a helicene‐like dication, helquat1, has been accomplished. Starting with gram scale of the racemic helquat1 sample, Dutch Resolution using family of 3 tartrate anions was key to achieve successful separation of M and P helical enantiomers of1 . Hundreds of milligrams of each enantiomer of this configurationally stable C2 ‐symmetric helquat have been obtained. Racemization barrier of1 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. Abstract : Racemic helquat1 has been resolved by using Dutch Resolution. Using family of three tartrate anion derivatives, hundreds of milligrams of each enantiomeric salt, [ P ‐1 ][Br]2 and [ M ‐1 ][Br]2, have been obtained in high optical purity (98% ee ). This is the first report on Dutch Resolution performed with a helicene‐like compound as well as the first such resolution with chiral quaternary ammonium cation.