Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes
Abstract The diverse utility of acyclic vinylsilanes has driven the interest in the synthesis of enantioenriched vinylsilanes bearing a Si-stereogenic center. However, the predominant approaches for catalytic asymmetric generation of Si-stereogenic vinylsilanes have mainly relied on transition metal...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-56232-y |
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| author | Kailin Yin Jinyu Zhang Deng Pan Shu-Han Chen Song Chen Yufeng Shi Genping Huang Dongbing Zhao |
| author_facet | Kailin Yin Jinyu Zhang Deng Pan Shu-Han Chen Song Chen Yufeng Shi Genping Huang Dongbing Zhao |
| author_sort | Kailin Yin |
| collection | DOAJ |
| description | Abstract The diverse utility of acyclic vinylsilanes has driven the interest in the synthesis of enantioenriched vinylsilanes bearing a Si-stereogenic center. However, the predominant approaches for catalytic asymmetric generation of Si-stereogenic vinylsilanes have mainly relied on transition metal-catalyzed reactions of alkynes with different silicon sources. Here we successfully realize the enantioselective synthesis of linear silicon-stereogenic vinylsilanes with good yields and enantiomeric ratios from simple alkenes under rhodium catalysis. The significance of this transformation lies in its ability to achieve regioconvergent and enantioconvergent conversion, efficiently transforming petroleum-derived isomeric mixtures of olefin feedstocks into a single regio- and stereoisomer product. The practicality of this method is further exemplified by the diverse downstream transformations of these enantioenriched silicon-stereogenic vinylsilanes leveraging the olefin functionality and the leaving group nature of the aryl substituent on silicon as well as the development of chiral π-conjugated double bond systems. |
| format | Article |
| id | doaj-art-57a02551ba38464fb037acfd2af9cb24 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-57a02551ba38464fb037acfd2af9cb242025-01-19T12:31:42ZengNature PortfolioNature Communications2041-17232025-01-0116111110.1038/s41467-025-56232-yEnantioselective construction of silicon-stereogenic vinylsilanes from simple alkenesKailin Yin0Jinyu Zhang1Deng Pan2Shu-Han Chen3Song Chen4Yufeng Shi5Genping Huang6Dongbing Zhao7State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, Nankai University 94 Weijin RoadState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, Nankai University 94 Weijin RoadDepartment of Chemistry, School of Science, Tianjin UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, Nankai University 94 Weijin RoadState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, Nankai University 94 Weijin RoadState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, Nankai University 94 Weijin RoadDepartment of Chemistry, School of Science, Tianjin UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, Nankai University 94 Weijin RoadAbstract The diverse utility of acyclic vinylsilanes has driven the interest in the synthesis of enantioenriched vinylsilanes bearing a Si-stereogenic center. However, the predominant approaches for catalytic asymmetric generation of Si-stereogenic vinylsilanes have mainly relied on transition metal-catalyzed reactions of alkynes with different silicon sources. Here we successfully realize the enantioselective synthesis of linear silicon-stereogenic vinylsilanes with good yields and enantiomeric ratios from simple alkenes under rhodium catalysis. The significance of this transformation lies in its ability to achieve regioconvergent and enantioconvergent conversion, efficiently transforming petroleum-derived isomeric mixtures of olefin feedstocks into a single regio- and stereoisomer product. The practicality of this method is further exemplified by the diverse downstream transformations of these enantioenriched silicon-stereogenic vinylsilanes leveraging the olefin functionality and the leaving group nature of the aryl substituent on silicon as well as the development of chiral π-conjugated double bond systems.https://doi.org/10.1038/s41467-025-56232-y |
| spellingShingle | Kailin Yin Jinyu Zhang Deng Pan Shu-Han Chen Song Chen Yufeng Shi Genping Huang Dongbing Zhao Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes Nature Communications |
| title | Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes |
| title_full | Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes |
| title_fullStr | Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes |
| title_full_unstemmed | Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes |
| title_short | Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes |
| title_sort | enantioselective construction of silicon stereogenic vinylsilanes from simple alkenes |
| url | https://doi.org/10.1038/s41467-025-56232-y |
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