Bimetallic Ru/Ru‐Catalyzed Asymmetric One‐Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones
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| Formato: | Artículo Open Access |
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Wiley
2024
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| _version_ | 1867019445019344896 |
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| author | Jingli He Zhaodi Li Ruhui Li Xuezhen Kou Delong Liu Wanbin Zhang |
| author_facet | Jingli He Zhaodi Li Ruhui Li Xuezhen Kou Delong Liu Wanbin Zhang Jingli He Zhaodi Li Ruhui Li Xuezhen Kou Delong Liu Wanbin Zhang |
| collection | Wiley Open Access |
| contents | Bimetallic Ru/Ru‐Catalyzed Asymmetric One‐Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones Jingli He Zhaodi Li Ruhui Li Xuezhen Kou Delong Liu Wanbin Zhang Advanced Science Abstract Asymmetric sequential hydrogenations of α ‐methylene γ ‐ or δ ‐keto carboxylic acids are established in one‐pot using a bimetallic Ru/Ru catalyst system, achieving the stereodivergent synthesis of all four stereoisomers of both chiral γ ‐ and δ ‐lactones with two non‐vicinal carbon stereocenters in high yields (up to 99%) and with excellent stereoselectivities (up to >99% ee and >20:1 dr). The compatibility of the two chiral Ru catalyst systems is investigated in detail, and it is found that the basicity of the reaction system plays a key role in the sequential hydrogenation processes. The protocol can be performed on a gram‐scale with a low catalyst loading (up to 11000 S/C) and the resulting products allow for many transformations, particularly for the synthesis of several key intermediates useful for the preparation of chiral drugs and natural products. 10.1002/advs.202400621 http://creativecommons.org/licenses/by/4.0/ |
| doi_str_mv | 10.1002/advs.202400621 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_advs_202400621 |
| institution | Wiley Open Access |
| license_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| publishDate | 2024 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Bimetallic Ru/Ru‐Catalyzed Asymmetric One‐Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones Jingli He Zhaodi Li Ruhui Li Xuezhen Kou Delong Liu Wanbin Zhang Advanced Science Bimetallic Ru/Ru‐Catalyzed Asymmetric One‐Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones Jingli He Zhaodi Li Ruhui Li Xuezhen Kou Delong Liu Wanbin Zhang Advanced Science Abstract Asymmetric sequential hydrogenations of α ‐methylene γ ‐ or δ ‐keto carboxylic acids are established in one‐pot using a bimetallic Ru/Ru catalyst system, achieving the stereodivergent synthesis of all four stereoisomers of both chiral γ ‐ and δ ‐lactones with two non‐vicinal carbon stereocenters in high yields (up to 99%) and with excellent stereoselectivities (up to >99% ee and >20:1 dr). The compatibility of the two chiral Ru catalyst systems is investigated in detail, and it is found that the basicity of the reaction system plays a key role in the sequential hydrogenation processes. The protocol can be performed on a gram‐scale with a low catalyst loading (up to 11000 S/C) and the resulting products allow for many transformations, particularly for the synthesis of several key intermediates useful for the preparation of chiral drugs and natural products. 10.1002/advs.202400621 http://creativecommons.org/licenses/by/4.0/ |
| title | Bimetallic Ru/Ru‐Catalyzed Asymmetric One‐Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones |
| topic | Advanced Science |
| url | https://advanced.onlinelibrary.wiley.com/doi/10.1002/advs.202400621 |