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 Citations (Scopus)

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
StatePublished - Dec 1 1993

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Alkenes
Olefins
Electrons
Cyclopentanes
Atoms
Isomers
Derivatives

All Science Journal Classification (ASJC) codes

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

Cite this

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title = "2,2-Dihalovinylcyclopropanes as Highly Diastereoselective Three-Atom Addends in Phenylthio Radical Mediated Vinylcyclopentane Synthesis",
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.",
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2,2-Dihalovinylcyclopropanes as Highly Diastereoselective Three-Atom Addends in Phenylthio Radical Mediated Vinylcyclopentane Synthesis. / Feldman, Ken S.; Berven, Heidi M.; Weinreb, Paul H.

In: Journal of the American Chemical Society, Vol. 115, No. 24, 01.12.1993, p. 11364-11369.

Research output: Contribution to journalArticle

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T1 - 2,2-Dihalovinylcyclopropanes as Highly Diastereoselective Three-Atom Addends in Phenylthio Radical Mediated Vinylcyclopentane Synthesis

AU - Feldman, Ken S.

AU - Berven, Heidi M.

AU - Weinreb, Paul H.

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N2 - 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.

AB - 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.

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