Issue 7, 2022

Transition metal-free selective C–S bond cleavage of Ugi-adducts for rapid preparation of peptidomimetics

Abstract

A transition metal-free C–S bond cleavage and subsequent Mannich reaction of Ugi-adducts with alcohols as well as thiols is developed. Diverse novel peptidomimetics containing N,O- or N,S-aminals are synthesized in a rapid, highly efficient and step-economical fashion. This method features exclusive selectivity, broad substrate scope, excellent yield and functional group tolerance, and was applied on substrates derived from the pharmaceuticals febuxostat, probenecid and memantine.

Graphical abstract: Transition metal-free selective C–S bond cleavage of Ugi-adducts for rapid preparation of peptidomimetics

Supplementary files

Article information

Article type
Communication
Submitted
27 nov. 2021
Accepted
10 mars 2022
First published
11 mars 2022

Green Chem., 2022,24, 2783-2787

Transition metal-free selective C–S bond cleavage of Ugi-adducts for rapid preparation of peptidomimetics

C. Liu, L. Song, V. A. Peshkov and E. V. Van der Eycken, Green Chem., 2022, 24, 2783 DOI: 10.1039/D1GC04421D

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