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Dostęp zamkniętyLarger scale Stahl oxidation with instant Cu removal in convenient synthesis of chiral bidentate N–heterocyclic carbene precursor
| cris.lastimport.scopus | 2024-02-12T20:27:52Z |
| dc.abstract.en | Commercially available N-Boc protected L-proline can be efficiently converted into a chiral, bidentate, aminoalkyl N-heterocyclic carbene ligand precursor in high yield (50% total after 4 steps) without column chromatography purification at any moment. The developed synthetic path includes: (1) redox step leading to an aldehyde, (2) imine condensation and in situ reduction to 1,2-diamine; (3) heterocyclization; (3) removal of the protecting group. Instant separation of Cu traces after the key Stahl oxidation at gram-scale was facilitated by the use of bis(isocyanide) scavenger, SnatchCat, forming insoluble, easy to remove RNC:→[Cu] complexes that allowed usto obtain crude intermediate suitably pure for next steps without tedious purification. |
| dc.affiliation | Uniwersytet Warszawski |
| dc.contributor.author | Szczepaniak, Grzegorz |
| dc.contributor.author | Nogaś, Wojciech |
| dc.contributor.author | Grela, Karol |
| dc.contributor.author | Grudzień, Krzysztof |
| dc.date.accessioned | 2024-01-25T04:59:29Z |
| dc.date.available | 2024-01-25T04:59:29Z |
| dc.date.issued | 2021 |
| dc.description.finance | Publikacja bezkosztowa |
| dc.description.volume | 199 |
| dc.identifier.doi | 10.1016/J.POLY.2021.115090 |
| dc.identifier.issn | 0277-5387 |
| dc.identifier.uri | https://repozytorium.uw.edu.pl//handle/item/110872 |
| dc.identifier.weblink | https://api.elsevier.com/content/article/PII:S0277538721000723?httpAccept=text/xml |
| dc.language | eng |
| dc.pbn.affiliation | chemical sciences |
| dc.relation.ispartof | Polyhedron |
| dc.relation.pages | 115090 |
| dc.rights | ClosedAccess |
| dc.sciencecloud | nosend |
| dc.subject.en | Amino acids |
| dc.subject.en | Chiral ligands |
| dc.subject.en | Metal scavengers |
| dc.subject.en | N-heterocyclic carbenes |
| dc.subject.en | Organic synthesis |
| dc.title | Larger scale Stahl oxidation with instant Cu removal in convenient synthesis of chiral bidentate N–heterocyclic carbene precursor |
| dc.type | JournalArticle |
| dspace.entity.type | Publication |