53253-07-9Relevant articles and documents
Abnormal Nazarov Reaction. A New Synthetic Approach to 2,3-Disubstituted 2-Cyclopentenones
Hirano, Shigeo,Takagi, Seiji,Hiyama, Tamejiro,Nozaki, Hitosi
, p. 169 - 173 (2007/10/02)
Acid-catalyzed reaction of β,β'-disubstituted cross conjugated dienones or the corresponding ethylene acetals gives mainly 2,3-disubstituted 2-cyclopentenones in stead of the simple Nazarov cyclization products, 3,4-disubstituted 2-cyclopentenones.This transformation is explained in terms of electrocyclic ring-closure, addition of hydroxylic solvent(s), tautomerization of the resulting 2-hydroxycyclopentanone intermediates, followed by solvolysis and isomerization.Based on this working hypothesis a new route to jasmonoids is disclosed which involves acid-treatment of the acyloin disilyl ethers derived from substituted glutarates.
