Addition of 2-oxazolidinones to arylidenecyclopropanes: A highly efficient method for the preparation of gem-aryl disubstituted homoallylic oxazolidinones

Amal Inoka Siriwardana, Kalum K A D S Kathriarachchi, Itaru Nakamura, Yoshinori Yamamoto

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The copper-catalyzed reaction of arylidenecyclopropanes (1) with 2-oxazolidinone (2) gave the corresponding homoallylic oxazolidinones (3) in good to high yields. For example, the reaction of diphenylmethylenecyclopropane (1a), bis(p-tolyl)methylenecyclopropane (1b), and bis(p-anisyl)methylene cyclopropane (1d) in the presence of 10 mol of Cu(OTf)(2) without solvent proceeded at 120 degrees C, giving the corresponding homoallylic oxazolidinones (3a, 3b, and 3d) in 89, 80, and 58 yields, respectively.
Original languageEnglish
Pages (from-to)333 - 339
Number of pages7
JournalHeterocycles
Volume66
Publication statusPublished - 2005
Externally publishedYes

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