Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions
An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azoliu...
| Main Authors: | , , , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2017
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/85620 http://hdl.handle.net/10220/43780 |
| _version_ | 1826111606692511744 |
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| author | Wu, Xingxing Liu, Bin Zhang, Yuexia Jeret, Martin Wang, Honglin Zheng, Pengcheng Yang, Song Song, Bao-An Chi, Yonggui Robin |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Wu, Xingxing Liu, Bin Zhang, Yuexia Jeret, Martin Wang, Honglin Zheng, Pengcheng Yang, Song Song, Bao-An Chi, Yonggui Robin |
| author_sort | Wu, Xingxing |
| collection | NTU |
| description | An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3-amino-acid derivatives. |
| first_indexed | 2024-10-01T02:53:11Z |
| format | Journal Article |
| id | ntu-10356/85620 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:53:11Z |
| publishDate | 2017 |
| record_format | dspace |
| spelling | ntu-10356/856202020-03-07T12:31:32Z Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions Wu, Xingxing Liu, Bin Zhang, Yuexia Jeret, Martin Wang, Honglin Zheng, Pengcheng Yang, Song Song, Bao-An Chi, Yonggui Robin School of Physical and Mathematical Sciences Cycloaddition Heterocycles An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3-amino-acid derivatives. NRF (Natl Research Foundation, S’pore) MOE (Min. of Education, S’pore) 2017-09-22T03:57:17Z 2019-12-06T16:07:14Z 2017-09-22T03:57:17Z 2019-12-06T16:07:14Z 2016 Journal Article Wu, X., Liu, B., Zhang, Y., Jeret, M., Wang, H., Zheng, P., et al. (2016). Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions. Angewandte Chemie International Edition, 55(40), 12280-12284. 1433-7851 https://hdl.handle.net/10356/85620 http://hdl.handle.net/10220/43780 10.1002/anie.201606571 en Angewandte Chemie International Edition © 2016 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim |
| spellingShingle | Cycloaddition Heterocycles Wu, Xingxing Liu, Bin Zhang, Yuexia Jeret, Martin Wang, Honglin Zheng, Pengcheng Yang, Song Song, Bao-An Chi, Yonggui Robin Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions |
| title | Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions |
| title_full | Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions |
| title_fullStr | Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions |
| title_full_unstemmed | Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions |
| title_short | Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions |
| title_sort | enantioselective nucleophilic β carbon atom amination of enals carbene catalyzed formal 3 2 reactions |
| topic | Cycloaddition Heterocycles |
| url | https://hdl.handle.net/10356/85620 http://hdl.handle.net/10220/43780 |
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