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

Geoffroy Hervé Lonca 1 Ciputra Tejo 2 Hui Ling Chan 2 Shunsuke Chiba 2 Fabien Gagosz 1, 3, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
2 Nanyang Technological University, School of Physical and Mathematical Sciences, Division of Chemistry and Biological Chemistry
3 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall
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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https://hal-polytechnique.archives-ouvertes.fr/hal-02091713
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Submitted on : Saturday, April 6, 2019 - 11:04:59 AM
Last modification on : Friday, April 12, 2019 - 1:31:50 AM

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

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