Enantioselective Friedel-Crafts Alkylation of Indoles, Pyrroles, and Furans with Trifluoropyruvate Catalyzed by Chiral Phosphoric Acid

被引：64
作者：
Kashikura, Wataru [1 ]
Itoh, Junji [1 ]
Mori, Keiji [1 ]
Akiyama, Takahiko [1 ]
机构：
[1] Gakushuin Univ, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2010年 / 5卷 / 03期
关键词：
alkylation; Bronsted acid; indoles; organofluorine compounds; trifluoropyruvate; 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; IMINES; CARBON; TRIFLUOROMETHYLATION; 4,7-DIHYDROINDOLES; HYDROPHOSPHONYLATION; ALDEHYDES; REAGENTS;
D O I：
10.1002/asia.200900481
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chiral phosphoric acid catalyzed Friedel-Crafts alkylation of indoles with 3, 3, 3-trifluoropyruvate gave the corresponding adducts in excellent yields with high enantioselectivities. Electron-deficient indoles, in particular, exhibited excellent enantioselectivities. (Chemical equation presented). © 2010 Wiley-VCH Verlag GmbH&Co. KGaA.
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收藏
页码：470 / 472
页数：3
相关论文
共 83 条
[1]   Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity [J].
Akiyama, T ;
Tamura, Y ;
Itoh, J ;
Morita, H ;
Fuchibe, K .
SYNLETT, 2006, (01) :141-143
[2]   Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].
Akiyama, T ;
Saitoh, Y ;
Morita, H ;
Fuchibe, K .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526
[3]   Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].
Akiyama, T ;
Morita, H ;
Itoh, J ;
Fuchibe, K .
ORGANIC LETTERS, 2005, 7 (13) :2583-2585
[4]   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
[5]  
AKIYAMA T, 2008, ACID CATALYSIS MODER, V1, P62
[6]   Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid [J].
Akiyama, Takahiko ;
Honma, Yasuhiro ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :399-402
[7]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[8]   Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].
Akiyama, Takahiko ;
Morita, Hisashi ;
Fuchibe, Kohei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071
[9]   Enantioselective Mannich-Type Reaction Catalyzed by a Chiral Phosphoric Acid Bearing an (S)-Biphenol Backbone [J].
Akiyama, Takahiko ;
Katoh, Takuya ;
Mori, Keiji ;
Kanno, Kazuaki .
SYNLETT, 2009, (10) :1664-1666
[10]   Enantioselective Robinson-Type Annulation Reaction Catalyzed by Chiral Phosphoric Acids [J].
Akiyama, Takahiko ;
Katoh, Takuya ;
Mori, Keiji .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4226-4228
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