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Methods for the enantioselective conversion of D-xylose to differentially protected myo-inositol and L-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI(2)-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.

synthesis

Synthesis of Differentially Protectedmyo- andchiro-Inositols from<scp>d</scp>-Xylose: Stereoselectivity in Intramolecular SmI2-Promoted Pinacol Reactions

Synthesis of Differentially Protectedmyo- andchiro-Inositols fromd-Xylose: Stereoselectivity in Intramolecular SmI2-Promoted Pinacol Reactions

Synthesis of Differentially Protectedmyo- andchiro-Inositols fromd-Xylose: Stereoselectivity in Intramolecular SmI₂-Promoted Pinacol Reactions