Issue 24, 2022

Ugi and Passerini reactions enable the incorporation of ΔAA into N-alkylated peptides and depsipeptides

Abstract

This work renders operational simplicity under mild conditions to synthesize some N-alkylated peptides and depsipeptides containing olefins. A sequential one-pot protocol merging a multicomponent reaction with oxidative elimination of phenylselenoxide allows the formation of α,β and β,γ olefin containing peptides and depsipeptides. Consequently, the regioselective construction of α,β-dehydrobutyrine and α,β-dehydro-homophenylalanine was possible using the Ugi four-component reaction; meanwhile, the Passerini three-component reaction produces the β-enamide preferably.

Graphical abstract: Ugi and Passerini reactions enable the incorporation of ΔAA into N-alkylated peptides and depsipeptides

Supplementary files

Article information

Article type
Paper
Submitted
29 Mac 2022
Accepted
12 Mei 2022
First published
12 Mei 2022

New J. Chem., 2022,46, 11502-11509

Ugi and Passerini reactions enable the incorporation of ΔAA into N-alkylated peptides and depsipeptides

O. Concepción, F. J. Peñaloza, J. J. López, G. Cabrera-Barjas, C. A. Jiménez, M. W. Paixão and A. F. de la Torre, New J. Chem., 2022, 46, 11502 DOI: 10.1039/D2NJ01545E

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