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Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2’‐Diamino‐1,1’‐binaphthalene in the Presence of Palladium Catalysts
Author(s) -
Pálinkás Noémi,
Mikle Gábor,
Aranyi Anita,
Péter Antal,
Kollár László
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002093
Subject(s) - chemistry , kinetic resolution , palladium , enantiomeric excess , aryl , enantiomer , axial chirality , atropisomer , catalysis , chirality (physics) , nucleophile , iodobenzene , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , alkyl , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
Palladium‐catalysed aminocarbonylation of iodobenzene and 1‐iodocyclohexene with both enantiomerically pure and racemic 2,2’‐diamino‐1,1’‐binaphthalene (BINAM) as N ‐nucleophile was carried out. The mono‐ and dicarboxamide enantiomers possessing axial chirality were synthesised using ( S ax )‐BINAM. In the possession of these reference compounds the partial chiral kinetic resolution of racemic BINAM was carried out using various optically active bidentate ligands such as ( 2S,4S )‐BDPP, ( 2S,3S )‐CHIRAPHOS and ( R )‐BINAP. It was revealed by chiral HPLC measurements that up to 10 % enantiomeric excess of carboxamides can be achieved in this way. Although with low enantioselection, enantioselectve aminocarbonylation was carried out for the first time.