NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines
Carboxylic esters can be readily obtained at low cost. Therefore, asymmetric catalytic activation of esters should provide useful strategies for organic synthesis. Here we report a N-heterocyclic carbene (NHC)-mediated reaction of α-aryl acetic esters with oxindole-derived α,β-unsaturated imines. Th...
| 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/10356/104221 http://hdl.handle.net/10220/19449 |
| _version_ | 1811693188302241792 |
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| author | Hao, Lin Chuen, Chan Wei Ganguly, Rakesh Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Hao, Lin Chuen, Chan Wei Ganguly, Rakesh Chi, Robin Yonggui |
| author_sort | Hao, Lin |
| collection | NTU |
| description | Carboxylic esters can be readily obtained at low cost. Therefore, asymmetric catalytic activation of esters should provide useful strategies for organic synthesis. Here we report a N-heterocyclic carbene (NHC)-mediated reaction of α-aryl acetic esters with oxindole-derived α,β-unsaturated imines. The reaction involves the formation of NHC-bound ester enolate intermediate from an ester as a key step, and furnishes spirocyclic oxindole products. The sterically congested spirocyclic oxindole bears a newly formed six-membered δ-lactams and cannot be easily prepared using other methods. |
| first_indexed | 2024-10-01T06:47:42Z |
| format | Journal Article |
| id | ntu-10356/104221 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:47:42Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1042212020-03-07T12:34:58Z NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines Hao, Lin Chuen, Chan Wei Ganguly, Rakesh Chi, Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry Carboxylic esters can be readily obtained at low cost. Therefore, asymmetric catalytic activation of esters should provide useful strategies for organic synthesis. Here we report a N-heterocyclic carbene (NHC)-mediated reaction of α-aryl acetic esters with oxindole-derived α,β-unsaturated imines. The reaction involves the formation of NHC-bound ester enolate intermediate from an ester as a key step, and furnishes spirocyclic oxindole products. The sterically congested spirocyclic oxindole bears a newly formed six-membered δ-lactams and cannot be easily prepared using other methods. 2014-05-26T02:33:31Z 2019-12-06T21:28:35Z 2014-05-26T02:33:31Z 2019-12-06T21:28:35Z 2013 2013 Journal Article Hao, L., Chuen, C. W., Ganguly, R., & Chi, Y. R. (2013). NHC-Catalyzed Ester Activation: Access to Sterically Congested Spirocyclic Oxindoles via Reaction of α-Aryl Esters and Unsaturated Imines. Synlett, 24(10), 1197–1200. 0936-5214 https://hdl.handle.net/10356/104221 http://hdl.handle.net/10220/19449 10.1055/s-0033-1338945 173632 en Synlett © 2013 Georg Thieme Verlag Stuttgart · New York. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Hao, Lin Chuen, Chan Wei Ganguly, Rakesh Chi, Robin Yonggui NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines |
| title | NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines |
| title_full | NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines |
| title_fullStr | NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines |
| title_full_unstemmed | NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines |
| title_short | NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines |
| title_sort | nhc catalyzed ester activation access to sterically congested spirocyclic oxindoles via reaction of α aryl esters and unsaturated imines |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/104221 http://hdl.handle.net/10220/19449 |
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