title: Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides.
abstract: 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.
authors.affiliation: 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.
authors.forename: Ihsan
authors.initials: I
authors.lastname: Erden
authors.forename: Nuket
authors.initials: N
authors.lastname: Ocal
authors.forename: Jiangao
authors.initials: J
authors.lastname: Song
authors.forename: Cindy
authors.initials: C
authors.lastname: Gleason
authors.forename: Christian
authors.initials: C
authors.lastname: Gärtner