Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles
Owing to the innovative applications of fluorinated compounds in many areas of technology and medicine, methods for the preparation of C-F quaternary fluorine containing compounds are in extremely high demand. Here, we report the discovery of a general procedure for an SN 2 reaction catalyzed by Pd/...
| Main Authors: | , , , , , , |
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| Format: | Journal Article |
| Sprog: | English |
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2020
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| Online adgang: | https://hdl.handle.net/10356/139358 |
| _version_ | 1826109752875155456 |
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| author | Zhu, Yi Mao, Yu Mei, Haibo Pan, Yi Han, Jianlin Soloshonok, Vadim A. Hayashi, Tamio |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Zhu, Yi Mao, Yu Mei, Haibo Pan, Yi Han, Jianlin Soloshonok, Vadim A. Hayashi, Tamio |
| author_sort | Zhu, Yi |
| collection | NTU |
| description | Owing to the innovative applications of fluorinated compounds in many areas of technology and medicine, methods for the preparation of C-F quaternary fluorine containing compounds are in extremely high demand. Here, we report the discovery of a general procedure for an SN 2 reaction catalyzed by Pd/Ding-SKP-type ligands, and that occurs between Colby pro-enolates with MBH carbonates to afford the corresponding products featuring two consecutive stereogenic carbons, including a C-F quaternary stereogenic center. The reactions readily occur at ambient temperatures with high chemical yields and in excellent chemo-, diastereo- and enantioselective manners. This practically attractive stereochemical outcome, coupled with the operational simplicity and structural generality, bodes well for the synthetic application of this process in the preparation of a novel class of biologically relevant fluorine-containing compounds. |
| first_indexed | 2024-10-01T02:23:27Z |
| format | Journal Article |
| id | ntu-10356/139358 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:23:27Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1393582020-05-19T04:56:47Z Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles Zhu, Yi Mao, Yu Mei, Haibo Pan, Yi Han, Jianlin Soloshonok, Vadim A. Hayashi, Tamio School of Physical and Mathematical Sciences Science::Chemistry Allylic Alkylations Enantioselectivity Owing to the innovative applications of fluorinated compounds in many areas of technology and medicine, methods for the preparation of C-F quaternary fluorine containing compounds are in extremely high demand. Here, we report the discovery of a general procedure for an SN 2 reaction catalyzed by Pd/Ding-SKP-type ligands, and that occurs between Colby pro-enolates with MBH carbonates to afford the corresponding products featuring two consecutive stereogenic carbons, including a C-F quaternary stereogenic center. The reactions readily occur at ambient temperatures with high chemical yields and in excellent chemo-, diastereo- and enantioselective manners. This practically attractive stereochemical outcome, coupled with the operational simplicity and structural generality, bodes well for the synthetic application of this process in the preparation of a novel class of biologically relevant fluorine-containing compounds. 2020-05-19T04:56:46Z 2020-05-19T04:56:46Z 2018 Journal Article Zhu, Y., Mao, Y., Mei, H., Pan, Y., Han, J., Soloshonok, V. A., & Hayashi, T. (2018). Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles. Chemistry - A European Journal, 24(36), 8994-8998. doi:10.1002/chem.201801670 0947-6539 https://hdl.handle.net/10356/139358 10.1002/chem.201801670 29683211 2-s2.0-85048998548 36 24 8994 8998 en Chemistry - A European Journal This is the accepted version of the following article: Zhu, Y., Mao, Y., Mei, H., Pan, Y., Han, J., Soloshonok, V. A., & Hayashi, T. (2018). Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles. Chemistry - A European Journal, 24(36), 8994-8998, which has been published in final form at dx.doi.org/10.1002/chem.201801670. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [https://authorservices.wiley.com/authorresources/Journal-Authors/licensing/self-archiving.html]. |
| spellingShingle | Science::Chemistry Allylic Alkylations Enantioselectivity Zhu, Yi Mao, Yu Mei, Haibo Pan, Yi Han, Jianlin Soloshonok, Vadim A. Hayashi, Tamio Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles |
| title | Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles |
| title_full | Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles |
| title_fullStr | Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles |
| title_full_unstemmed | Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles |
| title_short | Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles |
| title_sort | palladium catalyzed asymmetric allylic alkylations of colby pro enolates with mbh carbonates enantioselective access to quaternary c f oxindoles |
| topic | Science::Chemistry Allylic Alkylations Enantioselectivity |
| url | https://hdl.handle.net/10356/139358 |
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