First examples of nitrile ylid cycloadditions to α,β-unsaturated lactones

Pedro De March, Mustafa El Arrad, Marta Figueredo, Josep Font

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

Abstract

We have investigated the 1,3-dipolar cycloaddition of several nitrile yields to unsaturated five, six, and seven membered lactones. The cycloaddition proceeds effectively only with very electron-poor olefins. The αmethylene-γ-butyrolactone with an exocyclic double bond is the most reactive lactone. In all cases, exo adducts are obtained as major or exclusive products.
Original languageEnglish
Pages (from-to)11613-11622
JournalTetrahedron
Volume54
Issue number38
DOIs
Publication statusPublished - 17 Sep 1998

Keywords

  • Cycloaddition
  • Lactones
  • Nitrile ylids

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