| Autor: |
Lorenzo Carli, Anyawan Tapdara, Jianwen Jin, Yichao Zhao, Philip Wai Hong Chan |
| Jazyk: |
angličtina |
| Rok vydání: |
2023 |
| Předmět: |
|
| Zdroj: |
Tetrahedron Chem, Vol 7, Iss , Pp 100043- (2023) |
| Druh dokumentu: |
article |
| ISSN: |
2666-951X |
| DOI: |
10.1016/j.tchem.2023.100043 |
| Popis: |
A synthetic method for the preparation of 1,8-dihydroindeno[2,1-b]pyrroles and pyrrol-2-yl methanols in an enantioselective manner that relies on the chiral gold(I)-catalysed reactions of β-amino-1,4-enynols is described. A divergence in product selectivity was achieved by exploiting the electrostatic interactions between the chiral counteranion of the metal catalyst and the substrate. With a gold(I) complex containing a chiral N-triflyl phosphoramide-based counteranion, tandem dehydrative Nazarov-type electrocyclisation/hydroamination of the substrate was found to selectively occur to afford the indeno-fused pyrrole adduct. In contrast, changing to a chiral phosphate-based counteranion was observed to result in a hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation cascade pathway to give the 1H-pyrrole derivative. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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