Pd(II)-Catalyzed Enantioselective C-H Activation/C-O Bond Formation: Synthesis of Chiral Benzofuranones

被引:308
作者
Cheng, Xiu-Fen [1 ]
Li, Yan [1 ]
Su, Yi-Ming [1 ]
Yin, Feng [1 ]
Wang, Jian-Yong [1 ]
Sheng, Jie [1 ]
Vora, Harit U. [2 ]
Wang, Xi-Sheng [1 ]
Yu, Jin-Quan [2 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
NATURAL-PRODUCTS; PALLADIUM; FUNCTIONALIZATION; CYCLIZATION; C(SP(3))-H; AMINATION; COPPER; ACIDS; BENZOFURAN-2(3H)-ONES; DIBENZOFURANS;
D O I
10.1021/ja311259x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd(II)-catalyzed enantioselective C-H activation of phenylacetic acids followed by an intramolecular C-O bond formation afforded chiral benzofuranones. This reaction provides the first example of enantioselecctive C-H functionalizations through Pd(II)/Pd(IV) redox catalysis.
引用
收藏
页码:1236 / 1239
页数:4
相关论文
共 71 条
[1]   Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters [J].
Albicker, Martin R. ;
Cramer, Nicolai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9139-9142
[2]  
ANACARDIO R, 1995, SYNTHESIS-STUTTGART, P831
[3]   Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation [J].
Anas, Saithalavi ;
Cordi, Alex ;
Kagan, Henri B. .
CHEMICAL COMMUNICATIONS, 2011, 47 (41) :11483-11485
[4]   Stereoselective anhydride openings [J].
Atodiresei, Luliana ;
Schiffers, Ingo ;
Bolm, Carsten .
CHEMICAL REVIEWS, 2007, 107 (12) :5683-5712
[5]   Innate and Guided C-H Functionalization Logic [J].
Brueckl, Tobias ;
Baxter, Ryan D. ;
Ishihara, Yoshihiro ;
Baran, Phil S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :826-839
[6]   Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters [J].
Cao, Yiming ;
Jiang, Xianxing ;
Liu, Luping ;
Shen, Fangfang ;
Zhang, Futing ;
Wang, Rui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9124-9127
[7]   Multiple approaches to enantiopure spirocyclic benzofuranones using organocatalytic cascade reactions [J].
Cassani, Carlo ;
Tian, Xu ;
Escudero-Adan, Eduardo C. ;
Melchiorre, Paolo .
CHEMICAL COMMUNICATIONS, 2011, 47 (01) :233-235
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   A chiral Lewis acid strategy for enantioselective allylic C-H oxidation [J].
Covell, Dustin J. ;
White, M. Christina .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6448-6451
[10]   Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Do, Hien-Quang ;
Shabashov, Dmitry .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086