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

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 CH 2Cl 2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional...

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Bibliographic Details
Published in:Tetrahedron 2006-11, Vol.62 (46), p.10676-10682
Main Authors: Erden, Ihsan, Öcal, Nüket, Song, Jiangao, Gleason, Cindy, Gärtner, Christian
Format: Article
Language:English
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Summary: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 CH 2Cl 2 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.07.107