Synthesis of β-(Hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones

D. M. Hodgson; E. P. A. Talbot; B. P. Clark

doi:10.1055/s-0030-1260730

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Synfacts 2011(8): 0888-0888
DOI: 10.1055/s-0030-1260730

Metal-Mediated Synthesis

Synthesis of β-(Hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones

Contributor(s): Paul Knochel, Thomas Kunz
D. M. Hodgson*, E. P. A. Talbot, B. P. Clark
University of Oxford and Eli Lilly and Co. Ltd., Windlesham, UK

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Publication History

Publication Date:
20 July 2011 (online)

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Significance

A synthetic procedure for the preparation of β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones is reported. In the presence of zinc or a chromium(II) source, the readily available 3-(bromomethyl)furan-2(5H)-one reacts with an aldehyde to give the title compounds in good yields and high diastereoselectivities.