Indium-Mediated Reaction of 1-Bromo-1-nitroalkanes with Aldehydes: Access to 2-Nitroalkan-1-ols

[摘要]：A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane with a variety of aldehydes is reported. The reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroalkan-1-ols. The use of chiral sugar-derived aldehydes furnished the corresponding 2-nitroalkan-1-ols with excellent stereoselectivity. The utility of the novel sugar-derived 2,2-dialkyl-2-nitroalkan-1-ols for the preparation of branched iminosugar derivatives was demonstrated by the preparation of a hydroxymethyl branched polyhydroxylated azepane.

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