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Title

C-C bond formation by sequential intramolecular hydrogen atom transfer/intermolecular radical allylation reaction in carbohydrate systems

AuthorsLeón, Elisa I. ; Martín, Ángeles ; Pérez-Martín, Inés ; Quintanal, Luís M.; Suárez, Ernesto
KeywordsCarbohydrates
Radical reactions
Hydrogen transfer
Radical all­ylation
C–C coupling
Issue Date31-May-2012
PublisherWiley-VCH
CitationEuropean Journal of Organic Chemistry 2012(20): 3818- 3829 (2012)
AbstractA 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.
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.201200300
URIhttp://hdl.handle.net/10261/199384
Identifiersdoi: 10.1002/ejoc.201200300
issn: 1434-193X
e-issn: 1099-0690
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