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If the fragmentation of methyl 5\u2010iodo\u2010<jats:sc>D<\/jats:sc>\u2010ribofuranoside is mediated by zinc\/catalytic indium in the presence of bromonitromethane, a separable mixture of a 1\u2010nitro\u20105\u2010hexene and a 1\u2010bromo\u20101\u2010nitro\u20105\u2010hexene is obtained in moderate yields with good diastereoselectivities. However, if the reaction is mediated by <jats:italic>n<\/jats:italic>BuLi in the presence of nitromethane, the corresponding 1\u2010nitro\u20105\u2010hexene is obtained as the only product in excellent yield and stereoselectivity in a one\u2010pot 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\u2010nitro\u20105\u2010hexenes or 1\u2010nitro\u20106\u2010heptenes.<\/jats:p>","DOI":"10.1002\/ejoc.201300362","type":"journal-article","created":{"date-parts":[[2013,6,10]],"date-time":"2013-06-10T05:27:52Z","timestamp":1370842072000},"page":"5022-5027","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Domino Reaction of Iodoglycosides: Synthesis of Carbohydrate\u2010Based Nitroalkenes"],"prefix":"10.1002","volume":"2013","author":[{"given":"Raquel G.","family":"Soengas","sequence":"first","affiliation":[]},{"given":"Artur M. 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