University of the Basque Country (UPV/EHU), Department of Organic Chemistry I, Joxe Mari Korta R&D Center, Avda. Tolosa 72, 20018, Donostia-San Sebastián, Spain.
ChemSusChem. 2018 Nov 23;11(22):3893-3898. doi: 10.1002/cssc.201802216. Epub 2018 Nov 2.
The Cu -catalyzed selective α-alkylation of α-amino acid and peptide derivatives with 2-alkyl-1,3-dioxolanes is reported. This oxidative coupling is distinguished by its site-specificity, high diastereoselectivity, and chirality preservation and exhibits absolute chemoselectivity for N-aryl glycine motifs over other amino acid units. Collectively, the method allows for the assembly of challenging quaternary centers, as well as compounds derived from natural products of high structural complexity, which may provide ample opportunities for late-stage functionalization of peptides.
本文报道了铜催化的α-氨基酸和肽衍生物与 2-烷基-1,3-二恶烷的选择性α-烷基化反应。这种氧化偶联具有位点特异性、高非对映选择性和手性保持的特点，并对 N-芳基甘氨酸基序表现出绝对的化学选择性，而对其他氨基酸单元则没有选择性。总的来说，该方法可以构建具有挑战性的季碳原子，以及具有高结构复杂性的天然产物衍生化合物，这可能为肽的后期功能化提供大量机会。
