Construction of bridged and fused ring systems via intramolecular michael reactions of vinylnitroso compounds

Ilia Korboukh, Praveen Kumar, Steven M. Weinreb

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

The first examples of intramolecular Michael-type reactions of in situ-formed vinylnitroso compounds with carbon nucleophiles are reported. This methodology has been used to prepare a variety of ring systems including [3.2.1]-, [2.2.2]-, and [2.2.1]-bridged carbobicyclic compounds, as well as a fused [5.5]-ring compound. Malonate anions have proven to be effective carbon nucleophiles in these conjugate addition reactions, and simple ester potassium enolates have also been successfully employed.

Original languageEnglish (US)
Pages (from-to)10342-10343
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number34
DOIs
StatePublished - Aug 29 2007

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Nucleophiles
Bridged-Ring Compounds
Carbon
Addition reactions
Anions
Potassium
Esters
Negative ions
malonic acid
Fused-Ring Compounds

All Science Journal Classification (ASJC) codes

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

Cite this

Korboukh, Ilia ; Kumar, Praveen ; Weinreb, Steven M. / Construction of bridged and fused ring systems via intramolecular michael reactions of vinylnitroso compounds. In: Journal of the American Chemical Society. 2007 ; Vol. 129, No. 34. pp. 10342-10343.
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Construction of bridged and fused ring systems via intramolecular michael reactions of vinylnitroso compounds. / Korboukh, Ilia; Kumar, Praveen; Weinreb, Steven M.

In: Journal of the American Chemical Society, Vol. 129, No. 34, 29.08.2007, p. 10342-10343.

Research output: Contribution to journalArticle

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