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New conjugated dienamides via palladium-catalyzed selective aminocarbonylation of enynes

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13 Scopus citations

Abstract

New conjugated dienamides have been synthesized effectively via palladium-catalyzed aminocarbonylation of enynes in the presence of various amines, diaminoalkanes, and aminoalcohols. The products have been utilized as substrates in alkoxycarbonylation reactions using methanol as the nucleophile and Pd(PPh 3) 2Cl 2 as the catalyst to afford novel ω-amidoesters in high yields and selectivities. Interestingly, the product obtained from the alkoxycarbonylation reaction of the dienamide product of enyne 1b was observed to undergo carbonylation of the α,β-double bond with respect to the carbonyl group and isomerization of the second isolated double bond.

Original languageEnglish
Pages (from-to)6535-6539
Number of pages5
JournalTetrahedron Letters
Volume53
Issue number48
DOIs
StatePublished - 28 Nov 2012

Keywords

  • Alkoxycarbonylation
  • Aminocarbonylation
  • Dienamides
  • Enyne
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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