Iodoalkene-based approach towards carboxamides of biological importance: aminocarbonylation of 2-iodobornene and 3-iodo-2- quinuclidene

László Horváth, Andrea Petz, Lászlo Kollár

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6 Citations (Scopus)

Abstract

The palladium-catalysed aminocarbonylation of 2-iodobornene and 3-iodo-2-quinuclidene, possessing iodo alkene functionality, resulted in the high-yielding synthesis of the corresponding carboxamide derivatives. The substrates were synthesised from camphor and 3-quinuclidone, respectively, via their hydrazones. The chemoselective homogeneous carbonylation reaction of synthetic value was carried out under mild reaction conditions. While the carbonylation of the 2- iodobornene was found to be a facile reaction with yields of synthetic interest, its isomer, 1-iodocamphene, formed in Wagner-Meervein rearrangement, remained intact under the same reaction conditions.

Original languageEnglish
Pages (from-to)54-60
Number of pages7
JournalLetters in Organic Chemistry
Volume7
Issue number1
DOIs
Publication statusPublished - Jan 1 2010

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Keywords

  • Camphor
  • Carbon monoxide
  • Iodoalkenes aminocarbonylation
  • Palladium
  • Quinuclidene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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