Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage
| Autor: | Yang Shi, Hongliang Wang, Yufeng Sun, Jiayan Cui, Shijia Yu, Xin Hong, Chenhui Chen, Jianbo Xie, Zhan Lu |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
0301 basic medicine
Allylic rearrangement Multidisciplinary Silanes Stereochemistry Chemistry Hydrosilylation Organic Chemistry Organic Synthesis Enantioselective synthesis 02 engineering and technology 021001 nanoscience & nanotechnology Article Catalysis Kinetic resolution 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology Stereospecificity Organic synthesis lcsh:Q 0210 nano-technology lcsh:Science Bond cleavage |
| Zdroj: | iScience, Vol 23, Iss 4, Pp-(2020) iScience |
| ISSN: | 2589-0042 |
| Popis: | 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. Graphical Abstract Highlights • Iron-catalyzed 1,5-hydrosilylation of VCPs via C-C bond cleavage was first established • Chiral allyl silanes and chiral VCPs were obtained with high enantioselectivity • Various chiral allylic derivatives were delivered from chiral Z-allylic silanes • A possible mechanism via an iron-silyl species was proposed Catalysis; Organic Chemistry; Organic Synthesis |
| Databáze: | OpenAIRE |
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