Gold( i )-catalyzed 6-endo-dig azide–yne cyclization: efficient access to 2H-1,3-oxazines - École polytechnique Access content directly
Journal Articles Chemical Communications Year : 2017

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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hal-02091713 , version 1 (06-04-2019)

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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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