- Deuterium-isotope study on the reductive ring opening of benzylidene acetals.
Deuterium-isotope study on the reductive ring opening of benzylidene acetals.
Organic & biomolecular chemistry (2011-09-17)
I-Chi Lee, Medel Manuel L Zulueta, Chi-Rung Shie, Susan D Arco, Shang-Cheng Hung
PMID21922112
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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