Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp(3))-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives
文献类型：期刊论文
| 作者 | Fan, Zhoulong2,3; Shu, Shiqi1; Ni, Jiabin2,3; Yao, Qizheng1; Zhang, Ao2,3
|
| 刊名 | ACS CATALYSIS
 |
| 出版日期 | 2016-02 |
| 卷号 | 6期号:2页码:769-774 |
| 关键词 | C(sp(3))-H activation adamantane rimantadine regioselectivity stereoselectivity |
| ISSN号 | 2155-5435 |
| DOI | 10.1021/acscatal.5b02483 |
| 文献子类 | Article |
| 英文摘要 | Stereoselective functionalization of the adamantyl bridge methylene C(sp(3))-H bonds is a rather appealing, yet challenging strategy due to the bulky and unactivated nature. Here we present a palladium-catalyzed C(sp(3))-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, optically pure arylated rimantadine derivatives have been synthesized in high regio- and diastereoselectivity that compound space for further pharmaceutical research. |
| WOS关键词 | ALPHA-AMINO-ACIDS ; C-H ACTIVATION ; CARBON-HYDROGEN BONDS ; ADAMANTANE DERIVATIVES ; MEDICINAL CHEMISTRY ; COUPLING REACTIONS ; PALLADIUM ; FLUORINATION ; CYCLOPROPANES ; ALKYLATION |
| 资助项目 | Chinese NSF[81430080] ; Chinese NSF[81125021] ; Major State Basic Research Development Program[2015CB910603] ; SIMM[CASIMM0120154002/2002] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000369774900035 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276162]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Zhang, Ao |
| 作者单位 | 1.China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, Synthet Organ & Med Chem Lab, Shanghai 201203, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Fan, Zhoulong,Shu, Shiqi,Ni, Jiabin,et al. Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp(3))-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives[J]. ACS CATALYSIS,2016,6(2):769-774. |
| APA | Fan, Zhoulong,Shu, Shiqi,Ni, Jiabin,Yao, Qizheng,&Zhang, Ao.(2016).Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp(3))-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives.ACS CATALYSIS,6(2),769-774. |
| MLA | Fan, Zhoulong,et al."Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp(3))-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives".ACS CATALYSIS 6.2(2016):769-774. |
入库方式： OAI收割
来源：上海药物研究所
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