Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage
Summary: An iron-catalyzed highly anti-Markovnikov selective, enantioselective hydrosilylation of vinylcyclopropanes with PhSiH3 was reported for the preparation of valuable chiral allylic silanes via stereospecific C-C bond cleavage. Simultaneously, difficultly prepared chiral VCPs could be also ob...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2020-04-01
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| Series: | iScience |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2589004220301693 |
| _version_ | 1811198935393370112 |
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| author | Chenhui Chen Hongliang Wang Yufeng Sun Jiayan Cui Jianbo Xie Yang Shi Shijia Yu Xin Hong Zhan Lu |
| author_facet | Chenhui Chen Hongliang Wang Yufeng Sun Jiayan Cui Jianbo Xie Yang Shi Shijia Yu Xin Hong Zhan Lu |
| author_sort | Chenhui Chen |
| collection | DOAJ |
| description | Summary: An iron-catalyzed highly anti-Markovnikov selective, enantioselective hydrosilylation of vinylcyclopropanes with PhSiH3 was reported for the preparation of valuable chiral allylic silanes via stereospecific C-C bond cleavage. Simultaneously, difficultly prepared chiral VCPs could be also obtained with moderate to excellent enantioselectivity via this kinetic resolution pathway. The chiral Z-allylic silanes could be converted to various chiral allylic derivatives. A possible mechanism via an iron-silyl species was proposed based on experimental and computational studies. : Catalysis; Organic Chemistry; Organic Synthesis Subject Areas: Catalysis, Organic Chemistry, Organic Synthesis |
| first_indexed | 2024-04-12T01:39:36Z |
| format | Article |
| id | doaj.art-6bd0a24d8ef84594ad2b28842c6974e4 |
| institution | Directory Open Access Journal |
| issn | 2589-0042 |
| language | English |
| last_indexed | 2024-04-12T01:39:36Z |
| publishDate | 2020-04-01 |
| publisher | Elsevier |
| record_format | Article |
| series | iScience |
| spelling | doaj.art-6bd0a24d8ef84594ad2b28842c6974e42022-12-22T03:53:14ZengElsevieriScience2589-00422020-04-01234Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond CleavageChenhui Chen0Hongliang Wang1Yufeng Sun2Jiayan Cui3Jianbo Xie4Yang Shi5Shijia Yu6Xin Hong7Zhan Lu8Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, China; Corresponding authorDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310058, China; Corresponding authorSummary: An iron-catalyzed highly anti-Markovnikov selective, enantioselective hydrosilylation of vinylcyclopropanes with PhSiH3 was reported for the preparation of valuable chiral allylic silanes via stereospecific C-C bond cleavage. Simultaneously, difficultly prepared chiral VCPs could be also obtained with moderate to excellent enantioselectivity via this kinetic resolution pathway. The chiral Z-allylic silanes could be converted to various chiral allylic derivatives. A possible mechanism via an iron-silyl species was proposed based on experimental and computational studies. : Catalysis; Organic Chemistry; Organic Synthesis Subject Areas: Catalysis, Organic Chemistry, Organic Synthesishttp://www.sciencedirect.com/science/article/pii/S2589004220301693 |
| spellingShingle | Chenhui Chen Hongliang Wang Yufeng Sun Jiayan Cui Jianbo Xie Yang Shi Shijia Yu Xin Hong Zhan Lu Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage iScience |
| title | Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage |
| title_full | Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage |
| title_fullStr | Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage |
| title_full_unstemmed | Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage |
| title_short | Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage |
| title_sort | iron catalyzed asymmetric hydrosilylation of vinylcyclopropanes via stereospecific c c bond cleavage |
| url | http://www.sciencedirect.com/science/article/pii/S2589004220301693 |
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