Domínguez Guillermo, Mujika Anje, Hernández Iker, Soloshonok Vadim A, Landa Aitor, Oiarbide Mikel
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 Donostia/San Sebastián, Spain.
Basque Foundation for Science, IKERBASQUE, Bilbao 48013, Spain.
J Org Chem. 2025 Aug 22;90(33):11910-11922. doi: 10.1021/acs.joc.5c01392. Epub 2025 Aug 7.
α-Amido sulfones () are widely applied as electrophilic aminoalkylation reagents. However, nonproductive sulfinate species are formed alongside. Here, we report that ethyl propiolate-promoted coupling of and gramines provides 3-sulfonylmethylindole aminals smoothly, thus establishing α-amido sulfones as dual donor/acceptor reagents with full atom incorporation on the target molecule. Simple adjustment of reactants loading allows one to revert the reaction outcome, leading to exclusive formation of 3-sulfonylmethylindoles instead.
α-酰胺基砜被广泛用作亲电氨基烷基化试剂。然而，同时会形成无活性的亚磺酸盐物种。在此，我们报道丙炔酸乙酯促进的α-酰胺基砜与禾本科碱的偶联反应能顺利提供3-磺酰基甲基吲哚胺化物，从而将α-酰胺基砜确立为双供体/受体试剂，且目标分子上实现了全原子掺入。简单调整反应物用量可使反应结果反转，从而专一性地生成3-磺酰基甲基吲哚。
