The Nazarov Cyclization

F. G. West*, O. Scadeng, Yen-Ku Wu, R. J. Fradette, S. Joy

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapterpeer-review

46 Scopus citations

Abstract

Although well established as a reliable method for forming new cyclopentenone rings from acyclic precursors, the Nazarov reaction has been the subject of substantial recent work. The effect of substituents on 1,4-dien-3-one precursors is discussed. Asymmetric methods are presented, including chirality transfer, chiral Lewis acids, and asymmetric organocatalysis. An overview is given of various 'interrupted' variants, in which cyclized intermediates undergo domino trapping reactions with either nucleophilic or electrophilic reagents. Finally, cyclization via alternative and unconventional precursors is described, including the vinylogous and iso-Nazarov reactions, transition metal activation of alkyne-containing substrates, and the aza-Nazarov reaction.

Original languageEnglish
Title of host publicationComprehensive Organic Synthesis
Subtitle of host publicationSecond Edition
PublisherElsevier Ltd
Pages827-866
Number of pages40
Volume5
ISBN (Print)9780080977430
DOIs
StatePublished - 1 Feb 2014

Keywords

  • Asymmetric
  • Catalysis
  • Cycloaddition
  • Cyclopentenone
  • Domino process
  • Electrocyclization
  • Metallo-Nazarov
  • Nazarov reaction
  • Piancatelli reaction

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