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Issue 20, 2012
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Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone

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Abstract

A zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous solvents was developed to provide an efficient route to α-methylene-γ-butyrolactone, which is synthetically very useful. The desired products were obtained in moderate to high yields in aqueous solvents. Excellent drs were achieved, among which the best diastereomeric ratios of products were found when water was used in the indium-mediated reaction, and THF–NH4Cl (sat, aq) (2 : 1) mixture in the zinc-mediated reaction. Furthermore, the allylation can be induced by chiral centers, especially those in the α-position, as a substrate-controlled reaction to obtain the enantioselective homoallylation alcohols.

Graphical abstract: Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone

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Publication details

The article was received on 24 Feb 2012, accepted on 31 Mar 2012 and first published on 03 Apr 2012


Article type: Communication
DOI: 10.1039/C2OB25397F
Citation: Org. Biomol. Chem., 2012,10, 3991-3998
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    Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone

    Y. Gao, X. Wang, L. Sun, L. Xie and X. Xu, Org. Biomol. Chem., 2012, 10, 3991
    DOI: 10.1039/C2OB25397F

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