Abnormal Nazarov reaction. A new synthetic approach to 2, 3-disubstituted 2-cyclopentenones

S Hirano, S Takagi, T Hiyama, H Nozaki

文献索引：Hirano, Shigeo; Takagi, Seiji; Hiyama, Tamejiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 1 p. 169 - 173

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被引用次数: 24

摘要

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, ...