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

✍ Scribed by Wei-Min Dai; Wing Leung Mak; Anxin Wu

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 205 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01172-2

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✦ Synopsis

Unsymmetrical divinyl alkoxyacetates (such as 7a) undergo a Eu(fod) 3 -catalyzed regiospeci®c 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.

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