Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp(3))-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives

doi:10.1021/acscatal.5b02483

	Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp(3))-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives
	Fan, Zhoulong 2,3; Shu, Shiqi 1; Ni, Jiabin 2,3; Yao, Qizheng 1; Zhang, Ao2,3
刊名	ACS CATALYSIS
	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.
资助项目	Chinese NSF[81430080] ; Chinese NSF[81125021] ; Major State Basic Research Development Program[2015CB910603] ; SIMM[CASIMM0120154002/2002]
WOS关键词	ALPHA-AMINO-ACIDS ; C-H ACTIVATION ; CARBON-HYDROGEN BONDS ; ADAMANTANE DERIVATIVES ; MEDICINAL CHEMISTRY ; COUPLING REACTIONS ; PALLADIUM ; FLUORINATION ; CYCLOPROPANES ; ALKYLATION
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000369774900035
内容类型	期刊论文
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.