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C–C Bond Formation by Sequential Intramolecular Hydrogen Atom Transfer/Intermolecular Radical Allylation Reaction in Carbohydrate Systems
Author(s) -
León Elisa I.,
Martín Ángeles,
PérezMartín Inés,
Quintanal Luís M.,
Suárez Ernesto
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200300
Subject(s) - chemistry , intramolecular force , intermolecular force , disaccharide , hydrogen atom , hydrogen bond , tandem , free radical reaction , carbohydrate , intramolecular reaction , surface modification , stereochemistry , radical , photochemistry , computational chemistry , molecule , organic chemistry , group (periodic table) , materials science , composite material
Abstract 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.