Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones
A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic nitrones from alkenyl oximes. DFT calculations of the reaction pathway suggested that this hydroamination could proceed through an unprecedented nucleophilic amination of the unactivated alkene by t...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2014
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/102850 http://hdl.handle.net/10220/19197 |
| _version_ | 1811693517108412416 |
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| author | Peng, Xingao Tong, Benny Meng Kiat Hirao, Hajime Chiba, Shunsuke |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Peng, Xingao Tong, Benny Meng Kiat Hirao, Hajime Chiba, Shunsuke |
| author_sort | Peng, Xingao |
| collection | NTU |
| description | A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic nitrones from alkenyl oximes. DFT calculations of the reaction pathway suggested that this hydroamination could proceed through an unprecedented nucleophilic amination of the unactivated alkene by the oxime nitrogen atom. The transition state of this reaction is stabilized by an ionic interaction between a metal cation such as K+ and the oxime oxygen and negatively charged alkene moiety. |
| first_indexed | 2024-10-01T06:52:56Z |
| format | Journal Article |
| id | ntu-10356/102850 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:52:56Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1028502020-03-07T12:31:21Z Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones Peng, Xingao Tong, Benny Meng Kiat Hirao, Hajime Chiba, Shunsuke School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic nitrones from alkenyl oximes. DFT calculations of the reaction pathway suggested that this hydroamination could proceed through an unprecedented nucleophilic amination of the unactivated alkene by the oxime nitrogen atom. The transition state of this reaction is stabilized by an ionic interaction between a metal cation such as K+ and the oxime oxygen and negatively charged alkene moiety. 2014-04-09T07:17:17Z 2019-12-06T21:01:10Z 2014-04-09T07:17:17Z 2019-12-06T21:01:10Z 2014 2014 Journal Article Peng, X., Tong, B. M. K., Hirao, H., & Chiba, S. (2014). Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones. Angewandte Chemie International Edition, 53(7), 1959-1962. 1433-7851 https://hdl.handle.net/10356/102850 http://hdl.handle.net/10220/19197 10.1002/anie.201308617 en Angewandte chemie international edition © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Peng, Xingao Tong, Benny Meng Kiat Hirao, Hajime Chiba, Shunsuke Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones |
| title | Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones |
| title_full | Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones |
| title_fullStr | Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones |
| title_full_unstemmed | Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones |
| title_short | Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones |
| title_sort | inorganic base mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/102850 http://hdl.handle.net/10220/19197 |
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