Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

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• 作者：Ihsan Erden ; Nü ; ket Ö ; cal ; Jiangao Song ; Cindy Gleason and Christian Gä ; rtner
• 刊名：Tetrahedron
• 出版年：2006
• 出版时间：13 November 2006
• 年：2006
• 卷：62
• 期：46
• 页码：10676-10682
• 全文大小：657 K

文摘

An unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH₂Cl₂ in a one-pot reaction. This methodology is 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 C-2.