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Updated: Sep 21, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
1,4-Asymmetric Induction in the Chromium(II)- and Indium-Mediated Coupling of Allyl Bromides to Aldehydes
Robert J. Maguire1, Johann Mulzer, Jan W. Bats
1Institut für Organische Chemie, J. W. Goethe-Universität Frankfurt, Marie-Curie-Strasse 11, D-60439 Frankfurt am Main, Germany.
Abstract:
A series of allyl bromides bearing an ethereal stereogenic substituent at C-2 were synthesized from methyl acrylate. These were coupled with a range of aldehydes under chromium(II) chloride-mediated conditions to afford syn-4-alkoxyalkan-1-ols in good yield and diastereoselectivity. The effect of altering the nature of the ethereal group and alkyl substituent upon the diastereoselectivity of the reaction was also investigated. The relative stereochemistry was proved by X-ray structure analysis. The work was extended to replace the chromium(II) chloride with indium metal, and this also afforded syn-4-alkoxyalkan-1-ols in good yield and diastereoselectivity.
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