异常的内过氧化物异构化反应：从饱和富烯内过氧化物便捷合成2-乙烯基-2-环戊烯酮的方法。
Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides.
作者信息
Erden Ihsan, Ocal Nuket, Song Jiangao, Gleason Cindy, Gärtner Christian
机构信息
San Francisco State University, Department of Chemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USAYildiz Technical University, Faculty of Arts and Sciences, Department of Chemistry, Davutpasa Campus, 34010, Merter-Istanbul, Turkey.
出版信息
Tetrahedron. 2006 Nov 13;62(46):10676-10682. doi: 10.1016/j.tet.2006.07.107.
An unusual peroxide base promoted isomerization was uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH(2)Cl(2) in a one-pot reaction. This methodology was applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C2.
发现了一种不寻常的过氧化物碱促进的异构化反应。富烯衍生的饱和内过氧化物在二氯甲烷中用DBU进行一锅反应处理后生成2-乙烯基-2-环戊烯酮。该方法被应用于二氢茉莉酮的简便合成。此外，位于C-6侧链上的官能团通过对烯酮部分的共轭进攻参与碱催化的异构化反应，生成在C2位带有氧杂环的2-环戊烯酮。
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