Lange Markus, Alistratov Nikita, Vilotijevic Ivan
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstrasse 10, 07743 Jena, Germany.
Org Biomol Chem. 2024 Aug 22;22(33):6684-6689. doi: 10.1039/d4ob01063a.
Picolines and quinaldines are valuable building blocks and intermediates in the synthesis of natural products and pharmaceuticals. Functionalization of the methyl group in picolines and quinaldines under mild conditions is challenging. We report that the concept of latent pronucleophiles enables Lewis base catalysed allylation of picolines and quinaldines with allylic fluorides starting from silylated picolines and quinaldines. Reactions afford enantioenriched allylation products when chiral Lewis base catalysts are used. The allylation products can be rapidly transformed to quinolizine-4-ones.
甲基吡啶和喹哪啶是天然产物和药物合成中有价值的结构单元和中间体。在温和条件下实现甲基吡啶和喹哪啶中甲基的官能团化具有挑战性。我们报道，潜在亲核试剂的概念能够实现从硅烷基化的甲基吡啶和喹哪啶出发，通过路易斯碱催化使其与烯丙基氟化物发生烯丙基化反应。使用手性路易斯碱催化剂时，反应可得到对映体富集的烯丙基化产物。烯丙基化产物能够快速转化为喹嗪 -4- 酮。
