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

Authors
Dai, WM Mak, WL Wu, AX
Citation
Wm. Dai et al., Eu(fod)(3)-catalyzed tandem regiospecific rearrangement of divinyl alkoxyacetates and Diels-Alder reaction, TETRAHEDR L, 41(36), 2000, pp. 7101-7105
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
36
Year of publication
2000
Pages
7101 - 7105
Database
ISI
SICI code
0040-4039(20000902)41:36<7101:ETRROD>2.0.ZU;2-Z
Abstract
Unsymmetrical divinyl alkoxyacetates (such as 7a) undergo a Eu(fod)(3)-cata lyzed regiospecific allylic rearrangement to form C-5-substituted (E)-2-eth oxy-1,3-dienes at room temperature. When the rearrangement of 7a was carrie d out in the presence of maleic anhydride, a tandem allylic rearrangement a nd Diels-Alder reaction occurred to give the adduct 11. Reactions of other dienophiles in this tandem procedure were examined. (C) 2000 Elsevier Scien ce Ltd. All rights reserved.