Asymmetric oxyamination by mean of ruthenium-catalyzed N-Acyl nitrene transfer reaction to olefines

[Display omitted] We found that (OC)ruthenium-salen complex 2d, bearing a 3,5-dichlorophenyl group at the C2″ position on the binaphthyl framework, catalyzed direct oxazoline formation from 4-methyl-1,2-dihydronaphthalenes and 3-methyl-1H-indenes using 3-(3-bromophenyl)-1,4,2-dioxazol-5-one 3f as th...

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Veröffentlicht in:Tetrahedron letters 2023-06, Vol.123, p.154542, Article 154542
Hauptverfasser: Hashimoto, Keigo, Watari, Tatsuya, Uchida, Tatsuya
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Sprache:eng
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Zusammenfassung:[Display omitted] We found that (OC)ruthenium-salen complex 2d, bearing a 3,5-dichlorophenyl group at the C2″ position on the binaphthyl framework, catalyzed direct oxazoline formation from 4-methyl-1,2-dihydronaphthalenes and 3-methyl-1H-indenes using 3-(3-bromophenyl)-1,4,2-dioxazol-5-one 3f as the nitrene source via direct oxyamination through the putative N-acyl ruthenium(nitrene) intermediate with almost complete chemoselectivity and good to high enantioselectivity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154542