The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-(tert-Butyl)-1H-pyrrole-2,5-dione( cas:4144-22-3 ) is researched.Quality Control of 1-(tert-Butyl)-1H-pyrrole-2,5-dione.Zhan, Bei-Bei; Li, Ya; Xu, Jing-Wen; Nie, Xing-Liang; Fan, Jun; Jin, Liang; Shi, Bing-Feng published the article 《Site-selective δ-C(sp3)-H alkylation of amino acids and peptides with maleimides via a six-membered palladacycle》 about this compound( cas:4144-22-3 ) in Angewandte Chemie, International Edition. Keywords: amino acid alkylation Michael peptide maleimide palladacycle hydrogen bond; peptide alkylation Michael type maleimide isoleucinol; alkylation mechanism palladacycle transition state Curti Hammett principle; alkylation; palladacycles; palladium; peptides; site selectivity. Let’s learn more about this compound (cas:4144-22-3).
The site-selective functionalization of unactivated C(sp3)-H bonds remains one of the greatest challenges in organic synthesis. Herein, we report on the site-selective δ-C(sp3)-H alkylation of amino acids and peptides with maleimides via a kinetically less favored six-membered palladacycle in the presence of more accessible γ-C(sp3)-H bonds. Exptl. studies revealed that C-H bond cleavage occurs reversibly and preferentially at γ-Me over δ-Me C-H bonds while the subsequent alkylation proceeds exclusively at the six-membered palladacycle that is generated by δ-C-H activation. The selectivity can be explained by the Curtin-Hammett principle. The exceptional compatibility of this alkylation with various oligopeptides renders this procedure valuable for late-stage peptide modifications. Notably, this process is also the first palladium(II)-catalyzed Michael-type alkylation reaction that proceeds through C(sp3)-H activation.
There are many compounds similar to this compound(4144-22-3)Quality Control of 1-(tert-Butyl)-1H-pyrrole-2,5-dione. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.
Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics