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Gold( i )-catalyzed 6-endo-dig azide–yne cyclization: efficient access to 2H-1,3-oxazines

Abstract : Denitrogenative 6-endo-dig azide-yne cyclization of α-propargyloxy-β-haloalkylazides was enabled by gold catalysis, thus providing 2H-1,3-oxazines. This rare cyclization mode in gold-catalyzed reactions of azide-yne substrates was demonstrated to be facilitated and controlled by electronic and resonance effects of the alkyne substituents. Molecular transformations of the as-prepared 2H-1,3-oxazines were also investigated.
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Contributor : Aurélien Arnoux Connect in order to contact the contributor
Submitted on : Saturday, April 6, 2019 - 11:04:59 AM
Last modification on : Wednesday, April 27, 2022 - 5:22:13 PM



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Geoffroy Hervé Lonca, Ciputra Tejo, Hui Ling Chan, Shunsuke Chiba, Fabien L. Gagosz. Gold( i )-catalyzed 6-endo-dig azide–yne cyclization: efficient access to 2H-1,3-oxazines. Chemical Communications, 2017, 53 (4), pp.736-739. ⟨10.1039/c6cc08397h⟩. ⟨hal-02091713⟩



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