Synthesis of 2-Pyrrolidinones by Palladium-Catalyzed [3+2] Cycloaddition of Isocyanates

Research output: Contribution to journalArticle

Abstract

Pd/DPEphos catalyzes the [3+2] cycloaddition of various alkyl isocyanates with 2-acetoxymethyl-3-allyltrimethylsilane as a synthetic equivalent of trimethylenemethane (TMM). Taking advantage of 2-acetoxymethyl-3-allyltrimethylsilane acting both as nucleophile as well as electrophile this reaction gives a convenient access to 5-ring lactams with an exocyclic alkene moiety. The formation of the β,γ-unsaturated 2-pyrrolidinones occurs without olefin isomerization and without epimerization of the stereogenic centers. Mechanistic investigations suggest an initial N-allylation of the isocyanate followed by nucleophilic ring closure furnishing the desired 2-pyrrolidinones.
Original languageEnglish
Pages (from-to)581-585
Number of pages5
JournalSynlett
Volume30
Issue number5
DOIs
Publication statusPublished - 2019

Keywords

  • allyl silanes
  • cycloaddition
  • heterocycles
  • isocyanates
  • lactams
  • palladium
  • Tsuji-Trost allylation

ASJC Scopus subject areas

  • Organic Chemistry

Fields of Expertise

  • Human- & Biotechnology

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