Eu(fod)(3)-catalyzed tandem regiospecific rearrangement of divinyl alkoxyacetates and Diels-Alder reaction

Unsymmetrical divinyl alkoxyacetates (such as 7a) undergo a Eu(fod)(3)-catalyzed regiospecific allylic rearrangement to form C-5-substituted (E)-2-ethoxy-1,3-dienes at room temperature. When the rearrangement of 7a was carried out in the presence of maleic anhydride, a tandem allylic rearrangement and Diels-Alder reaction occurred to give the adduct 11. Reactions of other dienophiles in this tandem procedure were examined. (C) 2000 Elsevier Science Ltd. All rights reserved