Rhodium‐Catalyzed Enantioselective Silylation of Cyclopropyl C−H Bonds
| العنوان: | Rhodium‐Catalyzed Enantioselective Silylation of Cyclopropyl C−H Bonds |
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| المؤلفون: | Taegyo Lee, John F. Hartwig |
| المصدر: | Angewandte Chemie (International ed. in English), vol 55, iss 30 |
| بيانات النشر: | Wiley, 2016. |
| سنة النشر: | 2016 |
| مصطلحات موضوعية: | Cyclopropanes, silylation, Silylation, chemistry.chemical_element, Stereoisomerism, 010402 general chemistry, Medicinal chemistry, 01 natural sciences, Article, Catalysis, C−H activation, Rhodium, Cyclopropane, chemistry.chemical_compound, Organic chemistry, C-H activation, Silanes, Chemistry, 010405 organic chemistry, Organic Chemistry, Enantioselective synthesis, asymmetric catalysis, General Chemistry, General Medicine, Carbon, 0104 chemical sciences, Intramolecular force, rhodium, Chemical Sciences, Hydrogen |
| الوصف: | We describe an enantioseleclive silylation of cyclopropanes catalyzed by a rhodium precursor and the bisphosphine (S)-DTBM-SEGPHOS. (Hydrido)silyl ethers, generated in situ by the dehydrogenative silylation of cyclopropylmethanols with diethylsilane, undergo asymmetric, intramolecular silylation of cyclopropyl C-H bonds in high yields with high enantiomeric excesses in the presence of the rhodium catalyst. The resulting enantioenriched oxasilolanes are suitable substrates for Tamao-Fleming oxidation to form cyclopropanols with conservation of the ee from the C-H bond silylation. Preliminary mechanistic data suggest that C-H cleavage is likely to be the turnover-limiting and enantioselectivity-determining step. |
| وصف الملف: | application/pdf |
| تدمد: | 1521-3757 0044-8249 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::cd5b598deeb89f4f0177e905137cddd1 https://doi.org/10.1002/ange.201603153 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....cd5b598deeb89f4f0177e905137cddd1 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15213757 00448249 |
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