Reagents with Hypervalent Iodine: Formation of Convenient Chiral Synthetic Intermediates by Fragmentation of Carbohydrate Anomeric Alkoxy Radicals

Cleavage of the C1C2 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.