Beilstein Journal of Organic Chemistry p. 1772 - 1777 (2016)
Update date:2022-07-30
Topics:
Huck, Lena
González, Juan F.
De La Cuesta, Elena
Menéndez, J. Carlos
A sequential three-component process is described, starting from 3-arylmethylene-2,5-piperazinediones and involving a one-pot sequence of reactions achieving regioselective opening of the 2,5-diketopiperazine ring and diastereoselective generation of an aziridine ring. This method allows the preparation of N-unprotected, trisubstituted aziridines bearing a peptide side chain under mild conditions. Their transformation into β-trifluoroacetamido-α-ketoamide and α,β-diketoamide frameworks was also achieved in a single step.
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