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

Green Chemistry Pub Date: 2022-03-11 DOI: 10.1039/D1GC04421D

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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