One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids

Iryna Oleksandrivna Lebedyeva, Suvendu Biswas, Kevin Goncalves, Sean M. Sileno, Ashton R. Jackson, Kunal Patel, Peter J. Steel, Alan R. Katritzky

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Monocarbonyl activation of 2,2-disubstituted malonic acids with benzotriazole leads to decarboxylation of one of the carboxy groups and formation of a C-H bond. Intermediate carbonyl benzotriazoles then readily acylate nucleophilic reagents and peptides resulting in libraries of conjugates and peptidomimetics.

Original languageEnglish (US)
Pages (from-to)11695-11698
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number37
DOIs
StatePublished - Jan 1 2014

Fingerprint

Acylation
Nucleophiles
Peptides
Chemical activation
Peptidomimetics
Acids
Decarboxylation
benzotriazole
malonic acid

Keywords

  • acylation
  • cleavage reactions
  • conjugates
  • decarboxylation
  • peptides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids. / Lebedyeva, Iryna Oleksandrivna; Biswas, Suvendu; Goncalves, Kevin; Sileno, Sean M.; Jackson, Ashton R.; Patel, Kunal; Steel, Peter J.; Katritzky, Alan R.

In: Chemistry - A European Journal, Vol. 20, No. 37, 01.01.2014, p. 11695-11698.

Research output: Contribution to journalArticle

Lebedyeva, IO, Biswas, S, Goncalves, K, Sileno, SM, Jackson, AR, Patel, K, Steel, PJ & Katritzky, AR 2014, 'One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids', Chemistry - A European Journal, vol. 20, no. 37, pp. 11695-11698. https://doi.org/10.1002/chem.201403529
Lebedyeva, Iryna Oleksandrivna ; Biswas, Suvendu ; Goncalves, Kevin ; Sileno, Sean M. ; Jackson, Ashton R. ; Patel, Kunal ; Steel, Peter J. ; Katritzky, Alan R. / One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 37. pp. 11695-11698.
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AU - Goncalves, Kevin

AU - Sileno, Sean M.

AU - Jackson, Ashton R.

AU - Patel, Kunal

AU - Steel, Peter J.

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