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Browsing by Author "Shie, Chi-Rung"

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    Deuterium-isotope study on the reductive ring opening of benzylidene acetals
    (2011)
    Lee, I-Chi
    ;
    Zulueta, Medel Manuel L.
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    Shie, Chi-Rung
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    Arco, Susan D.
    ;
    Hung, Shang-Cheng
    Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD(3) revealed a retentive stereoselectivity probably through the rare S(N)i (internal nucleophilic substitution) mechanism. An S(N)1-like mechanism occurs in the acid-promoted regioselective BD(3)center dot THF- or Et(3)SiD-reductive ring opening.