Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis
An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert β-sp3 carbons of saturated esters. T...
Saved in:
| Main Authors: | , , , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2020
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/138257 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| id |
sg-ntu-dr.10356-138257 |
|---|---|
| record_format |
dspace |
| spelling |
sg-ntu-dr.10356-1382572023-02-28T19:25:29Z Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis Liu, Bin Wang, Weihong Huang, Ruoyan Yan, Jiekuan Wu, Jichang Xue, Wei Yang, Song Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry NHC Catalyst Carboxylic Esters An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert β-sp3 carbons of saturated esters. The use of HOBt as an additive was found to significantly improve both yields and enantioselectivities of the reactions. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-30T00:50:35Z 2020-04-30T00:50:35Z 2018 Journal Article Liu, B., Wang, W., Huang, R., Yan, J., Wu, J., Xue, W., . . ., Chi, R. Y. (2018). Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis. Organic letters, 20(1), 260-263. doi:10.1021/acs.orglett.7b03650 1523-7060 https://hdl.handle.net/10356/138257 10.1021/acs.orglett.7b03650 29239615 2-s2.0-85040246325 1 20 260 263 en Organic letters © 2017 American Chemical Society. All rights reserved. This paper was published in Organic letters and is made available with permission of American Chemical Society. application/pdf |
| institution |
Nanyang Technological University |
| building |
NTU Library |
| continent |
Asia |
| country |
Singapore Singapore |
| content_provider |
NTU Library |
| collection |
DR-NTU |
| language |
English |
| topic |
Science::Chemistry::Organic chemistry NHC Catalyst Carboxylic Esters |
| spellingShingle |
Science::Chemistry::Organic chemistry NHC Catalyst Carboxylic Esters Liu, Bin Wang, Weihong Huang, Ruoyan Yan, Jiekuan Wu, Jichang Xue, Wei Yang, Song Jin, Zhichao Chi, Robin Yonggui Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis |
| description |
An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert β-sp3 carbons of saturated esters. The use of HOBt as an additive was found to significantly improve both yields and enantioselectivities of the reactions. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Liu, Bin Wang, Weihong Huang, Ruoyan Yan, Jiekuan Wu, Jichang Xue, Wei Yang, Song Jin, Zhichao Chi, Robin Yonggui |
| format |
Article |
| author |
Liu, Bin Wang, Weihong Huang, Ruoyan Yan, Jiekuan Wu, Jichang Xue, Wei Yang, Song Jin, Zhichao Chi, Robin Yonggui |
| author_sort |
Liu, Bin |
| title |
Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis |
| title_short |
Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis |
| title_full |
Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis |
| title_fullStr |
Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis |
| title_full_unstemmed |
Direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis |
| title_sort |
direct activation of β-sp3-carbons of saturated carboxylic esters as electrophilic carbons via oxidative carbene catalysis |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/138257 |
| _version_ |
1759854685484744704 |