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Issue 7, 1994
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Aromatic Claisen rearrangements in carbohydrates: stereocontrol of rearrangement rates in unsaturated sugar substrates

Abstract

A remarkable difference is observed in the rates of [3,3]-sigmatropic rearrangement of aryl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 1 and 2; the slower reactivity of the α-isomers is consistent with AM1 calculated transition state energetics of model systems.

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Article type: Paper
DOI: 10.1039/P29940001399
Citation: J. Chem. Soc., Perkin Trans. 2, 1994, 1399-1401
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    Aromatic Claisen rearrangements in carbohydrates: stereocontrol of rearrangement rates in unsaturated sugar substrates

    K. K. Balasubramanian, N. G. Ramesh, A. Pramanik and J. Chandrasekhar, J. Chem. Soc., Perkin Trans. 2, 1994, 1399
    DOI: 10.1039/P29940001399

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