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

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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.

OriginalsprogEngelsk
TidsskriftJournal of the American Chemical Society
Vol/bind141
Nummer30
Sider (fra-til)11821-11826
Antal sider6
ISSN0002-7863
DOI
StatusUdgivet - 2019

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