Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: Synthesis of multisubstituted furans

Alexander S. Dudnik, Vladimir Gevorgyan

Research output: Contribution to journalArticle

178 Citations (Scopus)

Abstract

(Chemical Equation Presented) Even fused furans can be prepared by cycloisomerization of substituted allenyl ketones. The cascade reaction involves a [1,2]-migration of alkyl or aryl groups in allenyl ketones as the key step. Facile reaction in the presence of cationic complexes, as well as migratory aptitude in the cycloisomerization of unsymmetrically substituted allenes, strongly supports an electrophilic mechanism for this transformation.

Original languageEnglish (US)
Pages (from-to)5195-5197
Number of pages3
JournalAngewandte Chemie - International Edition
Volume46
Issue number27
DOIs
StatePublished - Jul 17 2007
Externally publishedYes

Fingerprint

Furans
Ketones
Metals
propadiene

Keywords

  • Allenyl ketones
  • Furans
  • Gold
  • Lewis acids
  • Rearrangment

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Metal-catalyzed [1,2]-alkyl shift in allenyl ketones : Synthesis of multisubstituted furans. / Dudnik, Alexander S.; Gevorgyan, Vladimir.

In: Angewandte Chemie - International Edition, Vol. 46, No. 27, 17.07.2007, p. 5195-5197.

Research output: Contribution to journalArticle

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