The 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl auxiliary is effective in directing bromopropargyloxy additions to the olefinic bonds of vinylogous esters/carbonates; in the presence of AIBN and 1-ethylpiperidinium hypophosphite, the adducts undergo highly stereoselective reductive radical cyclisations in which quaternary carbon stereogenic centres are generated.
R. McCague, R. G. Pritchard, R. J. Stoodley and D. S. Williamson, Chem. Commun., 1998, 2691 DOI: 10.1039/A807930G
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