Tandem inter [4+2]/intra [3+2] cycloadditions. 8. Cycloadditions with unactivated dipolarophiles

Scott E. Denmark, C. B.W. Senanayake

Research output: Contribution to journalArticle

Abstract

The tandem intermolecular [4+2]/intramolecular [3+2] cycloaddition of nitroalkenes bearing a pendant olefin is presented. The success of the tandem process is remarkable in view of the potential for intramolecular reaction with the tethered alkene. Cycloadditions of di- and trisubstituted nitroalkenes bearing two- and three-methylene tethers which contain mono-, di- and trisubstituted olefins are described. In all cases the tandem process is high yielding (with n-butyl vinyl ether as the dienophile) and highly stereoselective. Hydrogenolysis of the resulting nitroso acetals leads cleanly to fused pyrrolidines in high yields.

Original languageEnglish (US)
Pages (from-to)11579-11600
Number of pages22
JournalTetrahedron
Volume52
Issue number35
DOIs
StatePublished - Aug 26 1996

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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