Chiral Counteranion Strategy for Asymmetric Oxidative C(sp3)-H/C(sp3)-H Coupling: Enantioselective α-Allylation of Aldehydes with Terminal Alkenes

被引：183
作者：
Wang, Pu-Sheng [1 ,2 ]
Lin, Hua-Chen [1 ,2 ]
Zhai, Yu-Jia [1 ,2 ]
Han, Zhi-Yong [1 ,2 ]
Gong, Liu-Zhu [1 ,2 ,3 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 45期
关键词：
allylic compounds; C-H activation; cross-coupling; enantioselectivity; palladium; SP(3) C-H; ALLYLIC ALKYLATION; TERTIARY-AMINES; HOMOALLYLIC DIAMINATION; CATALYSIS CONCEPT; PHOSPHORIC-ACID; METAL CATALYSIS; BOND-CLEAVAGE; ACTIVATION; ADJACENT;
D O I：
10.1002/anie.201408199
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first enantioselective alpha-allylation of aldehydes with terminal alkenes has been realized by combining asymmetric counteranion catalysis and palladium-catalyzed allylic C-H activation. This method can tolerate a wide scope of alpha-branched aromatic aldehydes and terminal alkenes, thus affording allylation products in high yields and with good to excellent levels of enantioselectivity. Importantly, the findings suggest a new strategy for the future creation of enantioselective C-H/C-H coupling reactions.
引用
收藏
页码：12218 / 12221
页数：4
相关论文
共 94 条
[1]  
Adair G, 2008, ALDRICHIM ACTA, V41, P31
[2]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[3]   Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].
Allen, Anna E. ;
MacMillan, David W. C. .
CHEMICAL SCIENCE, 2012, 3 (03) :633-658
[4]   ASYMMETRIC-SYNTHESIS OF ACIDS BY THE PALLADIUM-CATALYZED HYDROCARBOXYLATION OF OLEFINS IN THE PRESENCE OF (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL OR (S)-(+)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE [J].
ALPER, H ;
HAMEL, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2803-2804
[5]  
[Anonymous], 2004, ANGEW CHEM, V116, P560
[6]  
[Anonymous], 2014, Angew. Chem
[7]  
[Anonymous], 2012, ANGEW CHEM, P124
[8]   New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556
[9]  
Brak K., 2013, ANGEW CHEM, V125, P558
[10]   Asymmetric Ion-Pairing Catalysis [J].
Brak, Katrien ;
Jacobsen, Eric N. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :534-561
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