ChemInform Abstract: Enantioselective Synthesis of Nitrogen Derivatives by Allyl Grignard Addition on Optically Active Nitroalkanes.
Abstract
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ChemInform Abstract
The benzyloxynitropropane (I) reacts with 2-butenylmagnesium chloride ( II) in tetrahydrofuran to yield a mixture of the isomeric nitrones ( III) and (IV) which are separated by column chromatography. Reduction of (III) with sodium boranate in methanol leads to the formation of the chiral hydroxylamine (V). Analogously, the nitro compounds (VI) and (I) are converted to mixtures of the hydroxylamines (VII) and ( VIII), (X), and (XI) or (XIII) and (XIV) respectively.
