Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals
Disclosed herein is a new catalytic approach for an efficient access to cyclic β-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ-carbon atoms of α,β-unsaturated imines to enals by iminium organic catalysis. This highly chemo-...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/137752 |
| _version_ | 1811683312983343104 |
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| author | Luo, Guoyong Huang, Zhijian Zhuo, Shitian Mou, Chengli Wu, Jian Jin, Zhichao Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Luo, Guoyong Huang, Zhijian Zhuo, Shitian Mou, Chengli Wu, Jian Jin, Zhichao Chi, Robin Yonggui |
| author_sort | Luo, Guoyong |
| collection | NTU |
| description | Disclosed herein is a new catalytic approach for an efficient access to cyclic β-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ-carbon atoms of α,β-unsaturated imines to enals by iminium organic catalysis. This highly chemo- and stereo-selective reaction affords cyclic β-amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules. |
| first_indexed | 2024-10-01T04:10:45Z |
| format | Journal Article |
| id | ntu-10356/137752 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:10:45Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1377522023-02-28T19:46:32Z Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals Luo, Guoyong Huang, Zhijian Zhuo, Shitian Mou, Chengli Wu, Jian Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Amine Catalysis Cyclic β-Amino Acid Disclosed herein is a new catalytic approach for an efficient access to cyclic β-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ-carbon atoms of α,β-unsaturated imines to enals by iminium organic catalysis. This highly chemo- and stereo-selective reaction affords cyclic β-amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-13T07:10:58Z 2020-04-13T07:10:58Z 2019 Journal Article Luo, G., Huang, Z., Zhuo, S., Mou, C., Wu, J., Jin, Z., & Chi, R. Y. (2019). Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals. Angewandte Chemie International Edition, 58(48), 17189-17193. doi:10.1002/ange.201908896 1433-7851 https://hdl.handle.net/10356/137752 10.1002/anie.201908896 31545543 2-s2.0-85074666818 48 58 17189 17193 en Angewandte Chemie International Edition This is the peer reviewed version of the following article: Luo, G., Huang, Z., Zhuo, S., Mou, C., Wu, J., Jin, Z., & Chi, R. Y. (2019). Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals. Angewandte Chemie International Edition, 58(48), 17189-17193, which has been published in final form at https://doi.org/10.1002/anie.201908896. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry Amine Catalysis Cyclic β-Amino Acid Luo, Guoyong Huang, Zhijian Zhuo, Shitian Mou, Chengli Wu, Jian Jin, Zhichao Chi, Robin Yonggui Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals |
| title | Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals |
| title_full | Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals |
| title_fullStr | Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals |
| title_full_unstemmed | Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals |
| title_short | Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals |
| title_sort | access to cyclic β amino acids by amine catalyzed enantioselective addition of the γ carbon atoms of α β unsaturated imines to enals |
| topic | Science::Chemistry::Organic chemistry Amine Catalysis Cyclic β-Amino Acid |
| url | https://hdl.handle.net/10356/137752 |
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