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Acid-Catalyzed Nazarov Reaction Controlled by β-Alkoxy Groups

Mitsuru Shindo*, Kentaro Yaji, Taisuke Kita, Kozo Shishido

*Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan, Email:

M. Shindo, K. Yaji, T. Kita, K. Shishido, Synlett, 2007, 1096-1100.

DOI: 10.1055/s-2007-973900

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The acid-catalyzed Nazarov reaction of easily accessible β-alkoxy divinyl ketones provides 5-oxycyclopent-2-enones. The effects of the β-alkoxy group on the catalyst efficiency and the regioselectivity are based on the stabilization of the intermediates and the spontaneous elimination of the group followed by trapping.

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Key Words

Nazarov Cyclization, cyclopentenones, electrocyclic reactions, catalysis, Lewis acids, ynolates

ID: J60-Y2007-1180