Improved one-pot synthesis of styryl tetrahydrofurans and cyclohexanes by radical addition to β-nitrostyrenes in the presence of benzoyl peroxide

Yeong Jiunn Jang, Yuh Kuo Shih, Jing Yuan Liu, Wen Yu Kuo, Ching-Fa Yao

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

Stereoselective styryl derivatives have been prepared based on radical substitution (addition-elimination) of heterocycles or cyclohydrocarbons units to (E)-β-nitrostyrenes 1 using a common radical initiator benzoyl peroxide. High reactivity and selectivity with wide substrate scope were attained by using this easy methodology. The reactions using easily obtained and one-pot potential starting materials gave excellent trans-selectivity with medium to high yields in all cases. Synthetic utility of this approach has been demonstrated by the preparation of various trans-styryl derivatives.

Original languageEnglish
Pages (from-to)2123-2128
Number of pages6
JournalChemistry - A European Journal
Volume9
Issue number9
DOIs
Publication statusPublished - 2003 May 9

Keywords

  • Alkenes
  • Heterocycles
  • Peroxides
  • Radical reactions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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