Carbon Isotope Labeling Strategy for β-Amino Acid Derivatives via Carbonylation of Azanickellacycles

Anne Katrine Ravn, Maria B. T. Vilstrup, Peter Nørby, Dennis Ulsøe Nielsen, Kim Daasbjerg, Troels Skrydstrup

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

Abstract

A series of 4-membered azametallacycles have been prepared by the oxidative addition of Ni(0) with aziridines. Stoichiometric C-13-labeled carbon monoxide could be efficiently incorporated via Ni-C bond insertion to generate air stable and isolable cyclic Ni-acyl complexes. Upon subjection to a range of C-, N-, O-, and S-nucleophiles, C-13-labeled beta-amino acids and derivatives thereof, as well as beta-aminoketones, could be rapidly accessed. The methodology proved highly adaptable for the synthesis of the antidiabetic drug, sitagliptin, with a single carbon isotope label.

Original languageEnglish
JournalJournal of the American Chemical Society
Volume141
Issue30
Pages (from-to)11821-11826
Number of pages6
ISSN0002-7863
DOIs
Publication statusPublished - 2019

Keywords

  • OXIDATIVE-ADDITION
  • REDUCTIVE-ELIMINATION
  • PALLADIUM COMPLEXES
  • PEPTIDES
  • F-18-FLUORINATION
  • AMINOKETONES
  • GENERATION
  • AZIRIDINES
  • FOLDAMERS
  • CHEMISTRY

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