Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone
The activation of carbon–carbon (C–C) bonds is an effective strategy in building functional molecules. The C–C bond activation is typically accomplished via metal catalysis, with which high levels of enantioselectivity are difficult to achieve due to high reactivity of metal catalysts and the metal-...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2018
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| Online Access: | https://hdl.handle.net/10356/89159 http://hdl.handle.net/10220/46119 |
| _version_ | 1811696209941757952 |
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| author | Li, Bao-Sheng Wang, Yuhuang Jin, Zhichao Zheng, Pengcheng Ganguly, Rakesh Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Li, Bao-Sheng Wang, Yuhuang Jin, Zhichao Zheng, Pengcheng Ganguly, Rakesh Chi, Robin Yonggui |
| author_sort | Li, Bao-Sheng |
| collection | NTU |
| description | The activation of carbon–carbon (C–C) bonds is an effective strategy in building functional molecules. The C–C bond activation is typically accomplished via metal catalysis, with which high levels of enantioselectivity are difficult to achieve due to high reactivity of metal catalysts and the metal-bound intermediates. It remains largely unexplored to use organocatalysis for C–C bond activation. Here we describe an organocatalytic activation of C–C bonds through the addition of an NHC to a ketone moiety that initiates a C–C single bond cleavage as a key step to generate an NHC-bound intermediate for chemo- and stereo-selective reactions. This reaction constitutes an asymmetric functionalization of cyclobutenones using organocatalysts via a C–C bond activation process. Structurally diverse and multicyclic compounds could be obtained with high optical purities via an atom and redox economic process. |
| first_indexed | 2024-10-01T07:35:44Z |
| format | Journal Article |
| id | ntu-10356/89159 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:35:44Z |
| publishDate | 2018 |
| record_format | dspace |
| spelling | ntu-10356/891592023-02-28T19:35:43Z Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone Li, Bao-Sheng Wang, Yuhuang Jin, Zhichao Zheng, Pengcheng Ganguly, Rakesh Chi, Robin Yonggui School of Physical and Mathematical Sciences Chemical Bonding Organic Chemistry DRNTU::Science::Chemistry The activation of carbon–carbon (C–C) bonds is an effective strategy in building functional molecules. The C–C bond activation is typically accomplished via metal catalysis, with which high levels of enantioselectivity are difficult to achieve due to high reactivity of metal catalysts and the metal-bound intermediates. It remains largely unexplored to use organocatalysis for C–C bond activation. Here we describe an organocatalytic activation of C–C bonds through the addition of an NHC to a ketone moiety that initiates a C–C single bond cleavage as a key step to generate an NHC-bound intermediate for chemo- and stereo-selective reactions. This reaction constitutes an asymmetric functionalization of cyclobutenones using organocatalysts via a C–C bond activation process. Structurally diverse and multicyclic compounds could be obtained with high optical purities via an atom and redox economic process. NRF (Natl Research Foundation, S’pore) EDB (Economic Devt. Board, S’pore) Published version 2018-09-27T04:32:45Z 2019-12-06T17:19:11Z 2018-09-27T04:32:45Z 2019-12-06T17:19:11Z 2015 Journal Article Li, B.-S., Wang, Y., Jin, Z., Zheng, P., Ganguly, R., & Chi, Y. R. (2015). Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone. Nature Communications, 6, 6207-. doi:10.1038/ncomms7207 https://hdl.handle.net/10356/89159 http://hdl.handle.net/10220/46119 10.1038/ncomms7207 25652912 en Nature Communications © 2015 Macmillan Publishers Limited. This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ 5 p. application/pdf |
| spellingShingle | Chemical Bonding Organic Chemistry DRNTU::Science::Chemistry Li, Bao-Sheng Wang, Yuhuang Jin, Zhichao Zheng, Pengcheng Ganguly, Rakesh Chi, Robin Yonggui Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone |
| title | Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone |
| title_full | Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone |
| title_fullStr | Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone |
| title_full_unstemmed | Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone |
| title_short | Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone |
| title_sort | carbon carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone |
| topic | Chemical Bonding Organic Chemistry DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/89159 http://hdl.handle.net/10220/46119 |
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