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Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C–H oxidation
The ubiquitous nature of C-H bonds in organic molecules makes them attractive as a target for rapid complexity generation, but brings with it the problem of achieving selective reactions. In developing new methodology for C-H functionalization, alkenes are an attractive starting material due to thei...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4157638/ https://www.ncbi.nlm.nih.gov/pubmed/24451587 http://dx.doi.org/10.1038/nchem.1841 |
Sumario: | The ubiquitous nature of C-H bonds in organic molecules makes them attractive as a target for rapid complexity generation, but brings with it the problem of achieving selective reactions. In developing new methodology for C-H functionalization, alkenes are an attractive starting material due to their abundance and low cost. Here we describe the conversion of 1-alkenes into 1,4-diols. The method involves the installation of a Si,N-type chelating auxiliary group on the alkene followed by iridium catalyzed C-H silylation of an unactivated δ-C(sp(3))-H bond to produce an silolane intermediate. Oxidation of the C-Si bonds affords a 1,4-diol. The method is demonstrated to have broad scope and a good functional group compatibility by application to the selective 1,4-oxygenation of several natural products and derivatives. |
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