C-C bond formation by sequential intramolecular hydrogen atom transfer/intermolecular radical allylation reaction in carbohydrate systems
2012
León, Elisa I. | Martín, Ángeles | Pérez-Martín, Inés | Quintanal, Luis M. | Suárez, Ernesto | Gobierno de Canarias | Ministerio de Ciencia e Innovación (España)
A tandem 1,5-, 1,6- or 1,8-intramolecular hydrogen atom transfer (HAT)/intermolecular radical allylation using mono- or (1→4)-O-disaccharide models is described. It is a simple, sequential, stereocontrolled methodology for C-C bond formation by remote free radical functionalization, giving access to interesting carbohydrate structures carrying differently functionalized tethers. A tandem intramolecular hydrogen atom transfer (HAT)/intermolecular radical allylation is described. This process occurs by a completely regio- and stereoselective route that provides a simple methodology for C-C bond formation on remote positions without modifying the remainder of the carbohydrate.
Show more [+] Less [-]This work was supported by the Research Programs of the Gobierno de Canarias (SolSubC200801000192 and CTQ2010‐18244) of the Ministerio de Ciencia e Innovación, cofinanced by the Fondo Europeo de Desarrollo Regional (FEDER). I. P.‐M. thanks the Spanish Ministerio de Ciencia e Innovación for the Research Program PIE 200930I138. L. M. Q. thanks the Consejo Superior de Investigaciones Científicas (CSIC) (Program I3P) for fellowships.
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