Enantioselective Synthesis of Tetrahydropyrano[3,4-b]indoles Catalyzed by Chiral N-Triflyl Phosphoramide via Intramolecular Friedel-Crafts Alkylation Reaction

被引:20
作者
Zhang, Jun-Wei [1 ,2 ]
Cai, Quan [2 ]
Shi, Xiao-Xin [1 ]
Zhang, Wei [2 ]
You, Shu-Li [1 ,2 ]
机构
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
asymmetric catalysis; chiral Bronsted acids; N-triflyl phosphoramide; Friedel-Crafts; indoles; BRONSTED ACID; INDOLES; 4,7-DIHYDROINDOLES; HYDROARYLATION; MOTIF; DERIVATIVES; IMINES; ROUTE;
D O I
10.1055/s-0030-1260537
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient intramolecular enantioselective Friedel-Crafts alkylation reaction of indolyl enones utilizing chiral N-triflyl phosphoramide catalyst is described. Various tetrahydropyrano[3,4-b]indoles (THPI) have been afforded with excellent yields and up to 98% ee.
引用
收藏
页码:1239 / 1242
页数:4
相关论文
共 54 条
[1]   New versatile route to the synthesis of tetrahydro-β-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3 [J].
Agnusdei, M ;
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7126-7129
[2]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[3]   Highly Efficient Route to Functionalized Tetrahydrocarbazoles Using a Tandem Cross-Metathesis/Intramolecular-Hydroarylation Sequence [J].
An, Xiao-Lei ;
Chen, Jia-Rong ;
Li, Chang-Feng ;
Zhang, Fu-Gen ;
Zou, You-Quan ;
Guo, Ying-Cen ;
Xiao, Wen-Jing .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (10) :2258-2265
[4]   A journey across recent advances in catalytic and stereoselective alkylation of indoles [J].
Bandini, M ;
Melloni, A ;
Tommasi, S ;
Umani-Ronchi, A .
SYNLETT, 2005, (08) :1199-1222
[5]   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
[6]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[7]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[8]   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
[9]   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
[10]   Ru-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence [J].
Chen, Jia-Rong ;
Li, Chang-Feng ;
An, Xiao-Lei ;
Zhang, Ji-Ji ;
Zhu, Xiao-Yu ;
Xiao, Wen-Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) :2489-2492