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| LETTER | Synlett 2007: 1096-1100
DOI: 10.1055/s-2007-973900 |
© Georg Thieme Verlag Stuttgart · New York
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Acid-Catalyzed Nazarov Reaction Controlled by β-Alkoxy Groups
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| Mitsuru Shindo*a, Kentaro Yajib, Taisuke Kitac, Kozo Shishidoc |
a Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan
Fax: +81(92)5837875; e-Mail: shindo@cm.kyushu-u.ac.jp;
b Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan
c Institute for Health Biosciences, the University of Tokushima, Shomachi, Tokushima 770-8505, Japan
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Received
31 January 2007 |
Abstract
Acid-catalyzed Nazarov reaction of β-alkoxy divinyl ketones providing 5-oxycyclopent-2-enones has been developed. 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. The substrates are easily accessible using the torquoselective olefination of esters with ynolates. Key words
electrocyclic reactions - catalysis - cyclizations - Lewis acids - ynolates
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