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 mar 2022
First published
11 mar 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements