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Abstract
AbstractHerein we describe a tandem fragmentation/Henry reaction of iodoglycosides, which involves formation of a carbon–carbon double bond and a carbon–carbon single bond. If the fragmentation of methyl 5‐iodo‐D‐ribofuranoside is mediated by zinc/catalytic indium in the presence of bromonitromethane, a separable mixture of a 1‐nitro‐5‐hexene and a 1‐bromo‐1‐nitro‐5‐hexene is obtained in moderate yields with good diastereoselectivities. However, if the reaction is mediated by nBuLi in the presence of nitromethane, the corresponding 1‐nitro‐5‐hexene is obtained as the only product in excellent yield and stereoselectivity in a one‐pot synthetic protocol. This is a general methodology that can be applied to iodopyranoses and iodofuranoses with different protecting groups for the efficient preparation of highly functionalized 1‐nitro‐5‐hexenes or 1‐nitro‐6‐heptenes.
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