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
Palladium-catalysed aminocarbonylation of iodobenzene and 1-iodocyclohexene with both enantiomerically pure and racemic 2,2'-diamino-1,1'-binaphthalene (BINAM) asN-nucleophile was carried out. The mono- and dicarboxamide enantiomers possessing axial chirality were synthesised using (S-ax)-...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
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2020
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| Sorozat: | CHEMISTRYSELECT
5 No. 35 |
| doi: | 10.1002/slct.202002093 |
| mtmt: | 31625419 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/21133 |
| Tartalmi kivonat: | Palladium-catalysed aminocarbonylation of iodobenzene and 1-iodocyclohexene with both enantiomerically pure and racemic 2,2'-diamino-1,1'-binaphthalene (BINAM) asN-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. |
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| Terjedelem/Fizikai jellemzők: | 11048-11051 |
| ISSN: | 2365-6549 |