Stereoselective synthesis of (E)-4-alkylidenecyclopent-2-en-1-ones by a tandem ring closure-Michael addition-elimination

Authors
Ballini, R Bosica, G Fiorini, D Gil, MV Petrini, M
Citation
R. Ballini et al., Stereoselective synthesis of (E)-4-alkylidenecyclopent-2-en-1-ones by a tandem ring closure-Michael addition-elimination, ORG LETT, 3(9), 2001, pp. 1265-1267
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
9
Year of publication
2001
Pages
1265 - 1267
Database
ISI
SICI code
1523-7060(20010503)3:9<1265:SSO(BA>2.0.ZU;2-O
Abstract
[GRAPHICS] Reaction of (Z)-1,4-diketones with various functionalized nitroalkanes in t he presence of DBU gives 4-alkylidenecyclopent-2-en-1-ones with E selectivi ty, A cyclopentadienone intermediate is probably formed by intramolecular a ldol condensation, and this reacts with a nitroalkane giving a Michael addi tion-elimination.