Beng Timothy K, Moreno Antonio
Department of Chemistry, Central Washington University Ellensburg WA 98926 USA
RSC Adv. 2020 Feb 28;10(15):8805-8809. doi: 10.1039/c9ra10888b. eCollection 2020 Feb 27.
C1 benzylated isoquinoline derivatives constitute the core of benzylisoquinoline alkaloids (BIAs). However, their C4 congeners remain elusive. Here, we describe a diastereoselective, catalytic, and modular C(sp)-C(sp) coupling protocol wherein β-amino sp C-H bonds of readily affordable vicinally functionalized dihydroisoquinolones are replaced by sp C-benzyl bonds. The method provides expedient access to C4 quaternary and homobenzylic dihydroisoquinolones, which are attractive fragments for potential drug discovery.
C1苄基异喹啉衍生物构成苄基异喹啉生物碱（BIAs）的核心。然而，它们的C4同系物仍然难以捉摸。在此，我们描述了一种非对映选择性、催化且模块化的C(sp)-C(sp)偶联方案，其中易于获得的邻位官能化二氢异喹啉酮的β-氨基sp C-H键被sp C-苄基键取代。该方法提供了便捷的途径来合成C4季碳和高苄基二氢异喹啉酮，它们是潜在药物发现中具有吸引力的片段。
