Development of a Titanocene-Catalyzed Enyne Cyclization/Isocyanide Insertion Reaction

Scott C. Berk, Robert B. Grossman, Stephen L. Buchwald

Research output: Contribution to journalArticlepeer-review

111 Scopus citations

Abstract

The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol % of Cp2Ti(PMe3)2 in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.

Original languageEnglish
Pages (from-to)8593-8601
Number of pages9
JournalJournal of the American Chemical Society
Volume116
Issue number19
DOIs
StatePublished - Sep 1 1994

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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