Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenes
Abstract Multi-component multi-functionalization reactions involving active intermediates are powerful tools for rapidly generating a wide array of compounds. Metal carbynoids, with their distinct reactivity, hold great promise for developing synthetic methodologies. However, their application in ca...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-02-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-56446-0 |
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| author | Xiaoyan Yang Xiaoyu Zhou Wenhao Hu Yu Qian |
| author_facet | Xiaoyan Yang Xiaoyu Zhou Wenhao Hu Yu Qian |
| author_sort | Xiaoyan Yang |
| collection | DOAJ |
| description | Abstract Multi-component multi-functionalization reactions involving active intermediates are powerful tools for rapidly generating a wide array of compounds. Metal carbynoids, with their distinct reactivity, hold great promise for developing synthetic methodologies. However, their application in catalytic transfer reactions has been hindered by the limited availability of suitable precursors. In this study, we investigate the catalytic potential of α-halo Rh-carbenes, leveraging the concept of metal carbynoids in multi-functionalization reactions. Through a chiral phosphoric acid-catalyzed asymmetric trifunctionalization, we have developed a method for synthesizing a variety of chiral α-cyclic ketal β-amino esters with high yields and excellent enantioselectivity. Our extensive experimental and computational studies reveal that α-halo Rh-carbenes exhibit carbynoid properties, which facilitate the transformation into functionalized Fischer-type Rh-carbenes through the decomposition of the C-halo bond. |
| format | Article |
| id | doaj-art-9ae0dc3db67a4de692b86af71e59284d |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-9ae0dc3db67a4de692b86af71e59284d2025-02-09T12:46:12ZengNature PortfolioNature Communications2041-17232025-02-011611910.1038/s41467-025-56446-0Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenesXiaoyan Yang0Xiaoyu Zhou1Wenhao Hu2Yu Qian3State Key Laboratory of Anti-Infective Drug Discovery and Development, Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen UniversitySchool of Pharmaceutical and Chemical Engineering, Taizhou UniversityState Key Laboratory of Anti-Infective Drug Discovery and Development, Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen UniversityState Key Laboratory of Anti-Infective Drug Discovery and Development, Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen UniversityAbstract Multi-component multi-functionalization reactions involving active intermediates are powerful tools for rapidly generating a wide array of compounds. Metal carbynoids, with their distinct reactivity, hold great promise for developing synthetic methodologies. However, their application in catalytic transfer reactions has been hindered by the limited availability of suitable precursors. In this study, we investigate the catalytic potential of α-halo Rh-carbenes, leveraging the concept of metal carbynoids in multi-functionalization reactions. Through a chiral phosphoric acid-catalyzed asymmetric trifunctionalization, we have developed a method for synthesizing a variety of chiral α-cyclic ketal β-amino esters with high yields and excellent enantioselectivity. Our extensive experimental and computational studies reveal that α-halo Rh-carbenes exhibit carbynoid properties, which facilitate the transformation into functionalized Fischer-type Rh-carbenes through the decomposition of the C-halo bond.https://doi.org/10.1038/s41467-025-56446-0 |
| spellingShingle | Xiaoyan Yang Xiaoyu Zhou Wenhao Hu Yu Qian Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenes Nature Communications |
| title | Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenes |
| title_full | Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenes |
| title_fullStr | Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenes |
| title_full_unstemmed | Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenes |
| title_short | Asymmetric multi-component trifunctionalization reactions with α-Halo Rh-carbenes |
| title_sort | asymmetric multi component trifunctionalization reactions with α halo rh carbenes |
| url | https://doi.org/10.1038/s41467-025-56446-0 |
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