Issue 7, 2022
From the journal:

Green Chemistry

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

Chao Liu,a   Liangliang Song,*b   Vsevolod A. Peshkovcd  and  Erik V. Van der Eycken ORCID logo *ae  

* Corresponding authors

a Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, Belgium
E-mail: erik.vandereycken@kuleuven.be

b Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China
E-mail: liangliangsong@njfu.edu.cn

c College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou 215123, P. R. China

d Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan 010000, Republic of Kazakhstan

e Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, Russia

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

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Article information

DOI
https://doi.org/10.1039/D1GC04421D
Article type
Communication
Submitted
27 Nov 2021
Accepted
10 Mar 2022
First published
11 Mar 2022

Green Chem., 2022,24, 2783-2787

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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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