Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp3)–H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives,ACS Catalysis

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Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp3)–H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives
ACS Catalysis ( IF 11.3 ) Pub Date : 2015-12-31 00:00:00 , DOI: 10.1021/acscatal.5b02483
Zhoulong Fan ₁ , Shiqi Shu ₂ , Jiabin Ni ₁ , Qizheng Yao ₂ , Ao Zhang ₁

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Stereoselective functionalization of the adamantyl bridge methylene C(sp³)–H bonds is a rather appealing, yet challenging strategy due to the bulky and unactivated nature. Here we present a palladium-catalyzed C(sp³)–H arylation/hetereoarylation of the antivirus drug rimantadine with the picolinamide moiety as the bidentate directing group and a mono-N-protected amino acid (MPAA) as the ligand. Multisubstituted rimantadine substrates and diverse aryl/heteroaryl iodides are well tolerated, and a series of optically pure arylated rimantadine derivatives have been synthesized in high regio- and diastereoselectivity that provides ample compound space for further pharmaceutical research.

中文翻译：

配体促进的未激活的C（sp ³）–H键的Pd（II）催化功能化：芳基化的金刚烷胺衍生物的区域和立体选择性合成

金刚烷基桥亚甲基C（sp ³）-H键的立体选择性官能化是一个颇具吸引力的方法，但由于其体积大且未活化，因此具有挑战性。在这里，我们介绍了抗病毒药物金刚乙胺的钯催化的C（sp ³）–H芳基化/杂芳基化，其中吡啶啉酰胺部分为双齿导向基团，单-N保护氨基酸（MPAA）为配体。多取代金刚烷胺底物和各种芳基/杂芳基碘化物均具有良好的耐受性，并且已经以高区域和非对映体选择性合成了一系列光学纯的芳基化金刚烷胺衍生物，为进一步的药物研究提供了充足的化合物空间。

更新日期：2015-12-31

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