Deuterium-isotope study on the reductive ring opening of benzylidene acetals |
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| Authors: | Lee I-Chi Zulueta Medel Manuel L Shie Chi-Rung Arco Susan D Hung Shang-Cheng |
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| Institution: | Genomics Research Center, Academia Sinica, Taipei 115, Taiwan. |
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| Abstract: | 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)·THF- or Et(3)SiD-reductive ring opening. |
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