Synthesis of Highly Substituted Pyrroles via Nucleophilic Catalysis

Simbarashe Ngwerume, Jason E. Camp

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

A nucleophilic catalysis method providing a concise synthesis of di-, tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermol. addn. of oximes to activated alkynes and thermal rearrangement of the in situ generated O-vinyl oximes to form pyrroles that contain a functional group handle at the C3/C4 position.
Original languageEnglish
Pages (from-to)6271-6274
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number18
DOIs
Publication statusE-pub ahead of print - 18 Aug 2010

Keywords

  • oxime stereoselective prepn
  • ketone hydroxyamine hydrochloride diastereoselective condensation
  • pyrrole prepn
  • alkyne oxime regioselective intermol addn nucleophilic catalysis
  • vinyl oxime thermal rearrangement microwave irradn

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