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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetals / chemistry*
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Aluminum Compounds / chemistry
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Benzylidene Compounds / chemistry*
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Chemistry, Organic / methods*
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Deuterium / chemistry*
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Glycosylation
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Hydroxides / chemistry
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Lithium Compounds / chemistry
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Magnetic Resonance Spectroscopy
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Oxidation-Reduction
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Stereoisomerism
Substances
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Acetals
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Aluminum Compounds
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Benzylidene Compounds
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Hydroxides
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Lithium Compounds
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lithium aluminum hydride
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hydroxide ion
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Deuterium