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

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

DOI

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 - Jul 2019

    Research areas

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

See relations at Aarhus University Citationformats

ID: 162443639