Laboratory of Bioorganic Chemistry and Membrane Biophysics (L.O.B.O.), Department of Organic and Inorganic Chemistry , Universidad de Extremadura , 10071 Cáceres , Spain.
Org Lett. 2018 Jul 6;20(13):3875-3878. doi: 10.1021/acs.orglett.8b01462. Epub 2018 Jun 26.
Enols are used for the first time in a condensation with aldehydes and isocyanides to selectively give three- or pseudo-four-component adducts, depending on the reaction conditions. These new transformations have proven to be a convenient alternative for the synthesis of biologically relevant pyrrolidinones containing peptidic or pseudo-peptidic groups on carbon 3. More importantly, this work attests to the utility of heterocyclic enols containing conjugated electron-withdrawing groups as useful reagents in isocyanide-based multicomponent reactions.
烯醇首次用于与醛和异氰化物的缩合反应中,根据反应条件,选择性地得到三或假四元加合物。这些新的转化已被证明是合成含有肽或拟肽基团在 3 位的生物相关吡咯烷酮的一种方便替代方法。更重要的是,这项工作证明了含有共轭吸电子基团的杂环烯醇作为基于异氰化物的多组分反应中有用试剂的实用性。