1,4-Asymmetric Induction in the Chromium(II)- and Indium-Mediated Coupling of Allyl Bromides to Aldehydes
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (20) , 6936-6940
- https://doi.org/10.1021/jo960986o
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.Keywords
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