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

Geoffroy Hervé Lonca; Ciputra Tejo; Hui Ling Chan; Shunsuke Chiba; Fabien Gagosz

doi:10.1039/c6cc08397h

Journal articles

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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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

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

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

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