An efficient route for the synthesis of chiral conduritol-derivative carboxamides via palladium-catalyzed aminocarbonylation of bromocyclohexenetetraols

Rui M.B. Carrilho, Viviana Heguaburu, Valeria Schapiro, Enrique Pandolfi, László Kollár, Mariette M. Pereira

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6 Citations (Scopus)

Abstract

A family of chiral conduritol-derivative carboxamides was synthesized through palladium-catalyzed aminocarbonylation of diastereoisomeric bromocyclohexenetetraols, previously prepared through biotransformation of bromobenzene by mutant strains of Pseudomonas putida F39/D. The coupling reactions of bromocyclohexenetetraols with CO and different amines, such as tert-butylamine, aniline, and piperidine, were performed in the presence of in situ generated Pd(0)/PPh 3 catalyst. The methodology was applied to the corresponding iodo-cyclohexenetetraol derivative, using (L)-alanine and (L)-valine methyl ethers as N-nucleophiles. The resulting carboxamides were obtained in highly chemoselective reactions, isolated, and fully characterized.

Original languageEnglish
Pages (from-to)6935-6940
Number of pages6
JournalTetrahedron
Volume68
Issue number34
DOIs
Publication statusPublished - Aug 26 2012

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Keywords

  • Aminocarbonylation
  • Carbon monoxide
  • Carboxamide
  • Conduritol
  • Glycomimic
  • Palladium
  • Vinyl-bromides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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