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Dutch Resolution of a configurationally stable [5]helquat
Author(s) -
Severa Lukáš,
Sázelová Petra,
Císařová Ivana,
Šaman David,
Koval Dušan,
Devadig Pradeep,
Kašička Václav,
Teplý Filip
Publication year - 2018
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22789
Subject(s) - chemistry , resolution (logic) , stereochemistry , combinatorial chemistry , artificial intelligence , computer science
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.