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...
Saved in:
| Main Authors: | , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2014
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/104220 http://hdl.handle.net/10220/19438 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| id |
sg-ntu-dr.10356-104220 |
|---|---|
| record_format |
dspace |
| spelling |
sg-ntu-dr.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. |
| institution |
Nanyang Technological University |
| building |
NTU Library |
| country |
Singapore |
| collection |
DR-NTU |
| language |
English |
| topic |
DRNTU::Science::Chemistry |
| 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 |
| 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. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Cheng, Jiajia Huang, Zhijian Chi, Robin Yonggui |
| format |
Article |
| author |
Cheng, Jiajia Huang, Zhijian Chi, Robin Yonggui |
| author_sort |
Cheng, Jiajia |
| title |
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_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_sort |
nhc organocatalytic formal lumo activation of α,β-unsaturated esters for reaction with enamides |
| publishDate |
2014 |
| url |
https://hdl.handle.net/10356/104220 http://hdl.handle.net/10220/19438 |
| _version_ |
1681038989186826240 |