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

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

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

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°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
Issue number1
DOIs
Publication statusPublished - 2005 Dec 31

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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