Indium-mediated reaction of nitroethane and aldehydes: characterization of the nucleophilic organoindium species
2012
Soengas, Raquel G. | Estévez, Amalia M.
A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane and 2-bromonitropropane with a variety of aldehydes was recently reported. Extension of the procedure to 1-bromo-1-nitroethane, which gives rise to a new chiral centre, was considered. On the basis of the diastereoselectivity of the nitroalkanols formed and NMR studies on the reaction mixtures, a mechanistic proposal for the indium-promoted reaction of bromonitroalkanes and aldehydes is discussed. The proposed mechanism allows the prediction of the stereochemical outcome of the present reaction.
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