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Elsevier, Tetrahedron: Asymmetry, 12(14), p. 1653-1658

DOI: 10.1016/s0957-4166(03)00274-x

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Synthesis of polyhydroxylated a-nitrocyclohexane carboxylic acids derived from D-glucose: a striking case of racemization

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Abstract

The first total synthesis of polyhydroxylated a-nitrocyclohexane carboxylic acids from sugars is reported. A salient aspect of the synthesis is an unexpected Henry-mediated racemization of this new class of highly functionalized cyclohexanes.