The effect of the carbon ligand on the reaction of organozinc reagents in the synthesis of substituted 2,5-dihydrofurans: A rare example of an uncatalysed allylic-substitution reaction involving alkyl zinc halides

Mark Woods, Nuno Monteiro, Geneviève Balme

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

Organozinc halides derived from Grignard reagents behave differently in their reaction with ethyl (±)-(2RS,3SR)-tetrahydro-4-methylene-2-phenyl-3- (phenylsulfonyl)furan-3-carboxylate (3) according to the hybridisation of the carbon ligand. During the development of short multi-component reactions for the synthesis of diverse functionalized ethyl 2,5-dihydrofuran-3-carboxylates it was discovered that aryl and vinyl zinc halides undergo clean reaction with 3 in the presence of Pd(PPh3)4. In contrast, when alkyl zinc halides are reacted with 3 in the presence of Pd(PPh3)4, reductive desulfonation of 3 is observed. Remarkably, in the absence of a transition metal catalyst, the allylic substitution of 3 with alkyl zinc halides proceeds cleanly and in moderate to good yield.

Original languageEnglish (US)
Pages (from-to)1711-1718
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number9
StatePublished - May 1 2000

Keywords

  • Catalysts
  • Heterocycles
  • Palladium
  • Sulfur
  • Zinc

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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