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 language | English |
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Pages (from-to) | 7655-7658 |
Number of pages | 4 |
Journal | Organic and Biomolecular Chemistry |
Volume | 9 |
Issue number | 22 |
DOIs | |
State | Published - 26 10 2011 |
Externally published | Yes |