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Synthesis 2008(19): 3148-3154
DOI: 10.1055/s-2008-1067259
DOI: 10.1055/s-2008-1067259
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Differentially Protected myo- and chiro-Inositols from d-Xylose: Stereoselectivity in Intramolecular SmI2-Promoted Pinacol Reactions
Further Information
Received
20 May 2008
Publication Date:
05 September 2008 (online)
Publication History
Publication Date:
05 September 2008 (online)
Abstract
Methods for the enantioselective conversion of d-xylose into differentially protected myo-inositol and l-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI2-promoted pinacol coupling. The stereoselectivity was extremely dependent on the conditions, suggesting a change in mechanism. Preliminary mechanistic experiments and possible explanations for this behavior are discussed.
Key words
inositol - pinacol - samarium - stereoselective - carbohydrates
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