Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester
An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lac...
| 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/10356/104214 http://hdl.handle.net/10220/19450 |
| _version_ | 1826118264177033216 |
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| author | Chen, Shaojin Hao, Lin Zhang, Yuexia Tiwari, Bhoopendra Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Chen, Shaojin Hao, Lin Zhang, Yuexia Tiwari, Bhoopendra Chi, Robin Yonggui |
| author_sort | Chen, Shaojin |
| collection | NTU |
| description | An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively. |
| first_indexed | 2024-10-01T04:40:51Z |
| format | Journal Article |
| id | ntu-10356/104214 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:40:51Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1042142020-03-07T12:34:58Z Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester Chen, Shaojin Hao, Lin Zhang, Yuexia Tiwari, Bhoopendra Chi, Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively. 2014-05-26T02:38:05Z 2019-12-06T21:28:30Z 2014-05-26T02:38:05Z 2019-12-06T21:28:30Z 2013 2013 Journal Article Chen, S., Hao, L., Zhang, Y., Tiwari, B., & Chi, Y. R. (2013). Asymmetric Access to the Smallest Enolate Intermediate via Organocatalytic Activation of Acetic Ester. Organic Letters, 15(22), 5822–5825. 1523-7060 https://hdl.handle.net/10356/104214 http://hdl.handle.net/10220/19450 10.1021/ol402877n 179774 en Organic letters © 2013 American Chemical Society. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Chen, Shaojin Hao, Lin Zhang, Yuexia Tiwari, Bhoopendra Chi, Robin Yonggui Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester |
| title | Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester |
| title_full | Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester |
| title_fullStr | Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester |
| title_full_unstemmed | Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester |
| title_short | Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester |
| title_sort | asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/104214 http://hdl.handle.net/10220/19450 |
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