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

30 Scopus citations

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

All Science Journal Classification (ASJC) codes

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

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