Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides |
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| Authors: | Erden Ihsan Ocal Nuket Song Jiangao Gleason Cindy Gärtner Christian |
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| Institution: | a San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA
b Yildiz Technical University, Faculty of Arts and Sciences, Department of Chemistry, Davutpasa Campus, 34010 Merter-Istanbul, Turkey |
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| Abstract: | 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. |
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