Studies on the chemoselectivity and diastereoselectivity of samarium(II) iodide mediated transformations of carbohydrate derived ω-halo-α,β- unsaturated easters

Article abstract of DOI:10.1016/S0040-4020(98)00191-4

Some carbohydrate derived ω-bromo- and ω-iode- α,β-unsaturated esters were reduced with SmI₂ under a variety of conditions. The chemoselectivity varies dramatically with the choice of solvent system, the identity of halogen atom, the type of ester used, the geometry of the double bond, and the oxygenation pattern of the substrate. The stereoselectivity of the SmI₂ mediated reactions is also influenced by the reaction parameters.