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

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

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 reson...

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Bibliographic Details
Main Authors: Lonca, Geoffroy Hervé, Tejo, Ciputra, Chan, Hui-Ling, Chiba, Shunsuke, Gagosz, Fabien
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Regioselective Oxidation
Synthetic Applications
Online Access:https://hdl.handle.net/10356/154862
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Institution: Nanyang Technological University
Language: English
Description
Summary: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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