Relay Catalysis by a Ruthenium Complex-Chiral Bronsted Acid Binary Sytem for Ternary Reaction Sequence Involving Enantioselective Pictet-Spengler-Type Cyclization as the Key Step

被引:37
作者
Toda, Yasunori [1 ]
Terada, Masahiro [1 ,2 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, Sendai, Miyagi 9808578, Japan
关键词
asymmetric catalysis; isomerization; protonation; cyclization; phenols; HIGHLY SELECTIVE ISOMERIZATION; FRIEDEL-CRAFTS REACTION; N-ALLYLAMIDES; ASYMMETRIC HYDROGENATION; COOPERATIVE CATALYSIS; MANNICH REACTIONS; PHOSPHORIC-ACIDS; C-H; BOND; METAL;
D O I
10.1055/s-0032-1318302
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Relay catalysis for a ternary reaction sequence composed of double-bond isomerization, protonation of the double bond, and enantioselective Pictet-Spengler-type cyclization was accomplished using a binary catalytic system consisting of a ruthenium hydride complex and a chiral phosphoric acid as the chiral Bronsted acid catalyst.
引用
收藏
页码:752 / 756
页数:5
相关论文
共 78 条
[1]  
Adair G, 2008, ALDRICHIM ACTA, V41, P31
[2]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[3]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[4]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[5]   Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Bronsted acid catalyzed self-coupling of enamides [J].
Baudequin, Christine ;
Zamfir, Alexandru ;
Tsogoeva, Svetlana B. .
CHEMICAL COMMUNICATIONS, 2008, (38) :4637-4639
[6]   Ring-Closing Metathesis/Isomerization/Pictet-Spengler Cascade via Ruthenium/Chiral Phosphoric Acid Sequential Catalysis [J].
Cai, Quan ;
Liang, Xiao-Wei ;
Wang, Shou-Guo ;
Zhang, Jun-Wei ;
Zhang, Xiao ;
You, Shu-Li .
ORGANIC LETTERS, 2012, 14 (19) :5022-5025
[7]   Enantioselective Intramolecular Aza-Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids [J].
Cai, Quan ;
Zheng, Chao ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) :8666-8669
[8]   Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis [J].
Cai, Quan ;
Zhao, Zhuo-An ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (40) :7428-7431
[9]   Pd(II)/Bronsted Acid Catalyzed Enantioselective Allylic C-H Activation for the Synthesis of Spirocyclic Rings [J].
Chai, Zhuo ;
Rainey, Trevor J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (08) :3615-3618
[10]   Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation [J].
Chen, Qing-An ;
Gao, Kai ;
Duan, Ying ;
Ye, Zhi-Shi ;
Shi, Lei ;
Yang, Yan ;
Zhou, Yong-Gui .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (04) :2442-2448