Deuterium-isotope study on the reductive ring opening of benzylidene acetals

I. Chi Lee, Medel Manuel L. Zulueta, Chi Rung Shie, Susan D. Arco, Shang Cheng Hung*

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

18 Scopus citations

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 Ni (internal nucleophilic substitution) mechanism. An S N1-like mechanism occurs in the acid-promoted regioselective BD 3·THF- or Et 3SiD-reductive ring opening.

Original languageEnglish
Pages (from-to)7655-7658
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number22
DOIs
StatePublished - 26 10 2011
Externally publishedYes

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