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...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Online Access: | https://hdl.handle.net/10356/154862 |
| _version_ | 1811676731986149376 |
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| author | Lonca, Geoffroy Hervé Tejo, Ciputra Chan, Hui-Ling Chiba, Shunsuke Gagosz, Fabien |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Lonca, Geoffroy Hervé Tejo, Ciputra Chan, Hui-Ling Chiba, Shunsuke Gagosz, Fabien |
| author_sort | Lonca, Geoffroy Hervé |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T02:26:08Z |
| format | Journal Article |
| id | ntu-10356/154862 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:26:08Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1548622023-02-28T19:59:03Z Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines Lonca, Geoffroy Hervé Tejo, Ciputra Chan, Hui-Ling Chiba, Shunsuke Gagosz, Fabien School of Physical and Mathematical Sciences Science::Chemistry Regioselective Oxidation Synthetic Applications 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. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by funding from Ecole Polytechnique (for F. G.), Nanyang Technological University (for S. C.) and the Singapore Ministry of Education (Academic Research Fund Tier 2: MOE2013-T2-1-060 for S. C.). F. G. and S. C. are grateful to PHC Merlion grant (Project 5.02.15) for the support of this collaboration project. 2022-01-17T02:04:25Z 2022-01-17T02:04:25Z 2017 Journal Article Lonca, G. H., Tejo, C., Chan, H., Chiba, S. & Gagosz, F. (2017). Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines. Chemical Communications, 53(4), 736-739. https://dx.doi.org/10.1039/c6cc08397h 1359-7345 https://hdl.handle.net/10356/154862 10.1039/c6cc08397h 27990524 2-s2.0-85008884209 4 53 736 739 en MOE2013-T2-1-060 Chemical Communications © 2017 The Royal Society of Chemistry. All rights reserved. This paper was published in Chemical Communications and is made available with permission of The Royal Society of Chemistry. application/pdf |
| spellingShingle | Science::Chemistry Regioselective Oxidation Synthetic Applications Lonca, Geoffroy Hervé Tejo, Ciputra Chan, Hui-Ling Chiba, Shunsuke Gagosz, Fabien Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines |
| title | Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines |
| title_full | Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines |
| title_fullStr | Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines |
| title_full_unstemmed | Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines |
| title_short | Gold(I)-catalyzed 6-endo-dig azide–yne cyclization : efficient access to 2H-1,3-oxazines |
| title_sort | gold i catalyzed 6 endo dig azide yne cyclization efficient access to 2h 1 3 oxazines |
| topic | Science::Chemistry Regioselective Oxidation Synthetic Applications |
| url | https://hdl.handle.net/10356/154862 |
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