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Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol

Remote functionalization of hydrocarbons could be achieved through successive zirconocene-mediated allylic C–H bond activations followed by a selective C–C bond cleavage. Determination of the reaction mechanism by density functional theory (DFT) calculations shows that the high stereocontrol observe...

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Detalles Bibliográficos
Autores principales: Vasseur, Alexandre, Perrin, Lionel, Eisenstein, Odile, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5654413/
https://www.ncbi.nlm.nih.gov/pubmed/29142680
http://dx.doi.org/10.1039/c5sc00445d
Descripción
Sumario:Remote functionalization of hydrocarbons could be achieved through successive zirconocene-mediated allylic C–H bond activations followed by a selective C–C bond cleavage. Determination of the reaction mechanism by density functional theory (DFT) calculations shows that the high stereocontrol observed in this process results from a large number of energetically accessible equilibria feeding a preferred reactive channel that leads to the major product. A distinctive consequence of this pattern is that stereoselectivity is enhanced upon heating.