2,2-Dihalovinylcyclopropanes as Highly Diastereoselective Three-Atom Addends in Phenylthio Radical Mediated Vinylcyclopentane Synthesis

Ken S. Feldman, Heidi M. Berven, Paul H. Weinreb

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

2,2-Dichloro- or 2,2-dibromovinylcyclopropane was condensed with electron-deficient alkenes in a phenylthio radical catalyzed process to afford 4-substituted and 4,5-disubstituted-l,l-dihalo-3-vinylcyclopentane derivatives in good yield and with good-to-excellent diastereoselectivity for the 3,4-cis isomer. Neither electron-rich nor β-substituted alkenes led to good yields of cyclopentane products. The diastereoselectivity and reactivity profiles of these transformations are satisfactorily rationalized by application of existing transition-state models of radical reactions.

Original languageEnglish (US)
Pages (from-to)11364-11369
Number of pages6
JournalJournal of the American Chemical Society
Volume115
Issue number24
DOIs
Publication statusPublished - Dec 1 1993

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this