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 L. Gagosz (1, 3)

1 DCSO - Laboratoire de synthèse organique
2 Nanyang Technological University [Singapour]
3 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall

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.

Domains: Chemical Sciences; Organic chemistry

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⟩