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A Tin‐Free Regioselective Radical De‐ O ‐benzylation by an Intramolecular Hydrogen Atom Transfer on Carbohydrate Templates
Author(s) -
Attouche Angie,
Urban Dominique,
Beau JeanMarie
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301783
Subject(s) - intramolecular force , regioselectivity , chemistry , tin , template , hydrogen atom , carbohydrate , photochemistry , stereochemistry , catalysis , organic chemistry , materials science , nanotechnology , group (periodic table)
Radically selective : A remarkable 1,7‐hydrogen atom transfer of a benzylic hydrogen atom to an O‐silylmethylene radical initiates a regioselective de‐ O ‐benzylation of benzylated saccharides. The reaction terminates by an ionic mechanism and is general for hydroxy benzylated substrates having a variety of functional groups.