DOAJ Open Access 2023

Chiral counteranion controlled chemoselectivity in gold catalysed hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation of β-amino-1,4-enynols

Lorenzo Carli Anyawan Tapdara Jianwen Jin Yichao Zhao Philip Wai Hong Chan

Abstrak

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.

Topik & Kata Kunci

Organic chemistry

Penulis (5)

Lorenzo Carli

Anyawan Tapdara

Jianwen Jin

Yichao Zhao

Philip Wai Hong Chan

Format Sitasi

APA MLA BibTeX

Carli, L., Tapdara, A., Jin, J., Zhao, Y., Chan, P.W.H. (2023). Chiral counteranion controlled chemoselectivity in gold catalysed hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation of β-amino-1,4-enynols. https://doi.org/10.1016/j.tchem.2023.100043

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Informasi Jurnal

Tahun Terbit: 2023
Sumber Database: DOAJ
DOI: 10.1016/j.tchem.2023.100043
Akses: Open Access ✓