报告了一种通过三元合作催化介导的主导反应，实现S-(-)-5,6-二氢咔啉-4-酮的广谱不对称合成方法。在Jorgensen-Hayashi催化剂、碘化铜和Hunig碱的存在下，1-甲酰基-9H-β-咔啉与末端炔烃之间的反应通过多级串联途径进行，以优异的产率和优秀的ee值得到目标化合物。这些化合物显示出有趣的动力学特性，并被评估了其对疟疾寄生虫的体外抗疟活性。此外，5,6-二氢咔啉-4-酮被证明是合成不同融合的β-咔啉衍生物的多功能前体。
摘要：
An enantioselective synthesis of S-()-5,6-dihydrocanthin-4-ones via a triple cooperative catalysis-mediated domino reaction having a broad substrate scope is reported. The reaction between substituted 1-formyl-9H-β-carbolines and terminal alkynes in the presence of catalytic amounts of Jorgensen–Hayashi catalyst, copper iodide, and Hunig base proceeded via a multicascade route, affording the title compounds in good yields and excellent ees with interesting mechanistic features. These compounds were assessed for in vitro antiplasmodial activity against P. falciparum strains. Additionally, 5,6-dihydrocanthin-4-ones are demonstrated to be a versatile precursor to different fused β-carboline derivatives via simple synthetic transformations.
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