NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides
An effective wake-up call: Stable ,β-unsaturated esters were activated by the addition of a chiral N-heterocyclic carbene (NHC) organocatalyst, and the resulting reactive Michael acceptor intermediates reacted with enamide nucleophiles to furnish optically pure products (see scheme; Ts=p-toluenesulf...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2014
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/104220 http://hdl.handle.net/10220/19438 |
| _version_ | 1811684162903474176 |
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| author | Cheng, Jiajia Huang, Zhijian Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Cheng, Jiajia Huang, Zhijian Chi, Robin Yonggui |
| author_sort | Cheng, Jiajia |
| collection | NTU |
| description | An effective wake-up call: Stable ,β-unsaturated esters were activated by the addition of a chiral N-heterocyclic carbene (NHC) organocatalyst, and the resulting reactive Michael acceptor intermediates reacted with enamide nucleophiles to furnish optically pure products (see scheme; Ts=p-toluenesulfonyl). These products can be converted readily into bioactive δ-lactams, piperidines, and their derivatives. |
| first_indexed | 2024-10-01T04:24:15Z |
| format | Journal Article |
| id | ntu-10356/104220 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:24:15Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1042202020-03-07T12:34:58Z NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides Cheng, Jiajia Huang, Zhijian Chi, Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry An effective wake-up call: Stable ,β-unsaturated esters were activated by the addition of a chiral N-heterocyclic carbene (NHC) organocatalyst, and the resulting reactive Michael acceptor intermediates reacted with enamide nucleophiles to furnish optically pure products (see scheme; Ts=p-toluenesulfonyl). These products can be converted readily into bioactive δ-lactams, piperidines, and their derivatives. 2014-05-26T01:29:53Z 2019-12-06T21:28:34Z 2014-05-26T01:29:53Z 2019-12-06T21:28:34Z 2013 2013 Journal Article Cheng, J., Huang, Z., & Chi, Y. R. (2013). NHC Organocatalytic Formal LUMO Activation of ,β-Unsaturated Esters for Reaction with Enamides. Angewandte Chemie International Edition, 52(33), 8592–8596. 1433-7851 https://hdl.handle.net/10356/104220 http://hdl.handle.net/10220/19438 10.1002/anie.201303247 173635 en Angewandte chemie international edition © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry Cheng, Jiajia Huang, Zhijian Chi, Robin Yonggui NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides |
| title | NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides |
| title_full | NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides |
| title_fullStr | NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides |
| title_full_unstemmed | NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides |
| title_short | NHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides |
| title_sort | nhc organocatalytic formal lumo activation of α β unsaturated esters for reaction with enamides |
| topic | DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/104220 http://hdl.handle.net/10220/19438 |
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