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Reagents with Hypervalent Iodine: Formation of Convenient Chiral Synthetic Intermediates by Fragmentation of Carbohydrate Anomeric Alkoxy Radicals
Author(s) -
de Armas Pedro,
Francisco Cosme G.,
Suárez Ernesto
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199207721
Subject(s) - hypervalent molecule , alkoxy group , chemistry , radical , anomer , reagent , bond cleavage , fragmentation (computing) , iodine , benzene , cleavage (geology) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , alkyl , materials science , composite material , fracture (geology) , computer science , operating system
Cleavage of the C1C2 bond in carbohydrates is achieved via the related alkoxy radicals by adding (diacetoxyiodo)benzene (DIB) to the substrate in the presence of iodine [Eq. (a)]. The course of the reaction is independent of the protecting groups R, the ring size, and the configuration of the substrate at C2. The cleavage products are valuable chiral building blocks.