Institute of Natural Sciences and Mathematics, Ural Federal University , 620000 Ekaterinburg, Russian Federation.
J Org Chem. 2017 Dec 1;82(23):12827-12833. doi: 10.1021/acs.joc.7b02193. Epub 2017 Nov 1.
Active methylene compounds react with in situ generated nonstabilized azomethine ylides via the domino Mannich reaction-dipolar cycloaddition to form 3,3-disubstituted pyrrolidines, including oxindole alkaloids. When the starting material possesses a single activated hydrogen, the reaction terminates at the Mannich base stage. The developed methodology was applied to a short and efficient synthesis of (±)-horsfiline and N-protected (±)-coerulescine.
活性亚甲基化合物与原位生成的未稳定亚胺叶立德通过多米诺曼尼希反应-环加成反应反应，形成 3,3-取代的吡咯烷，包括吲哚生物碱。当起始原料仅含有一个活泼氢时，反应终止于曼尼希碱阶段。所开发的方法学被应用于（±）-horsfiline 和 N-保护（±）-coerulescine 的短高效合成。
