Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines

被引：42
作者：
Vidal, Xandro [1 ,2 ]
Mascarenas, Jose L. [1 ,2 ]
Gulias, Moises [1 ,2 ]
机构：
[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela 15782, Spain
[2] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 05期
基金：
欧洲研究理事会;
关键词：
C-H FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; BOND ACTIVATION; 3+2 ANNULATION; 2-ALKENYLPHENOLS; BENZYLAMINES; IODINATION; LIGANDS; ACIDS;
D O I：
10.1021/jacs.8b12636
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Benzyl and allyltriflamides can engage in Pd-catalyzed oxidative (4+2) annulations with allenes, to produce highly valuable tetrahydroisoquinoline or dihydropyridine skeletons. The reaction is especially efficient when carried out in the presence of designed N-protected amino acids as metal ligands. More importantly, using this type of chiral ligands, it is possible to perform desymmetrizing, annulative C-H activations of prochiral diarylmethylphenyl amides, and thus obtain the corresponding isoquinolines with high enantiomeric ratios.
引用
收藏
页码：1862 / 1866
页数：5
相关论文
共 48 条
[1]   Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome [J].
Casanova, Noelia ;
Del Rio, Karina P. ;
Garcia-Fandino, Rebeca ;
Mascarenas, Jose L. ;
Gulias, Moises .
ACS CATALYSIS, 2016, 6 (05) :3349-3353
[2]   Rhodium-Catalyzed (5+1) Annulations Between 2-Alkenylphenols and Allenes: A Practical Entry to 2,2-Disubstituted 2H-Chromenes [J].
Casanova, Noelia ;
Seoane, Andres ;
Mascarenas, Jose L. ;
Gulias, Moises .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (08) :2374-2377
[3]   Palladium-Catalyzed Formal (5+2) Annulation between ortho-Alkenylanilides and Allenes [J].
Cendon, Borja ;
Casanova, Noelia ;
Comanescu, Cezar ;
Garcia-Fandino, Rebeca ;
Seoane, Andres ;
Gulias, Moises ;
Mascarenas, Jose L. .
ORGANIC LETTERS, 2017, 19 (07) :1674-1677
[4]   C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].
Chen, David Y. -K. ;
Youn, So Won .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474
[5]   Ligand-accelerated enantioselective methylene C(sp3)-H bond activation [J].
Chen, Gang ;
Gong, Wei ;
Zhuang, Zhe ;
Andra, Michal S. ;
Chen, Yan-Qiao ;
Hong, Xin ;
Yang, Yun-Fang ;
Liu, Tao ;
Houk, K. N. ;
Yu, Jin-Quan .
SCIENCE, 2016, 353 (6303) :1023-1027
[6]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295
[7]   Pd(II)-Catalyzed Enantioselective C-H Activation/C-O Bond Formation: Synthesis of Chiral Benzofuranones [J].
Cheng, Xiu-Fen ;
Li, Yan ;
Su, Yi-Ming ;
Yin, Feng ;
Wang, Jian-Yong ;
Sheng, Jie ;
Vora, Harit U. ;
Wang, Xi-Sheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1236-1239
[8]   Asymmetric Synthesis of Isoquinoline Alkaloids: 2004-2015 [J].
Chrzanowska, Maria ;
Grajewska, Agnieszka ;
Rozwadowska, Maria D. .
CHEMICAL REVIEWS, 2016, 116 (19) :12369-12465
[9]   Room-temperature enantioselective C-H iodination via kinetic resolution [J].
Chu, Ling ;
Xiao, Kai-Jiong ;
Yu, Jin-Quan .
SCIENCE, 2014, 346 (6208) :451-455
[10]   Pd-Catalyzed Enantioselective C-H Iodination: Asymmetric Synthesis of Chiral Diarylmethylamines [J].
Chu, Ling ;
Wang, Xiao-Chen ;
Moore, Curtis E. ;
Rheingold, Arnold L. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) :16344-16347
12345