Novel axially chiral bis-arylthiourea-based organocatalysts for asymmetric Friedel-Crafts type reactions

被引:133
作者
Fleming, Eimear M. [1 ]
McCabe, Thomas [1 ]
Connon, Stephen J. [1 ]
机构
[1] Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
关键词
D O I
10.1016/j.tetlet.2006.07.112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It has been shown that catalytic amounts (10-20 mol %) of novel axially chiral bis-arylthioureas promote the asymmetric organocatalytic Friedel-Crafts type addition of indole and N-methylindole to nitroolefins. The optimum catalyst is capable of promoting the reaction between challenging substrates such as N-methylindole and nitroolefins bearing aliphatic beta-substituents with enantioselectivity unprecedented for an organocatalytic system. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7037 / 7042
页数:6
相关论文
共 45 条
[1]   Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].
Austin, JF ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173
[2]   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
[3]   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
[4]   Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones [J].
Bandini, M ;
Fagioli, M ;
Melchiorre, P ;
Melloni, A ;
Umani-Ronchi, A .
TETRAHEDRON LETTERS, 2003, 44 (31) :5843-5846
[5]   Organocatalysis mediated by (thio)urea derivatives [J].
Connon, Stephen J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427
[6]   ACCELERATION OF A DIPOLAR CLAISEN REARRANGEMENT BY HYDROGEN-BONDING TO A SOLUBLE DIARYL UREA [J].
CURRAN, DP ;
KUO, LH .
TETRAHEDRON LETTERS, 1995, 36 (37) :6647-6650
[7]   ALTERING THE STEREOCHEMISTRY OF ALLYLATION REACTIONS OF CYCLIC ALPHA-SULFINYL RADICALS WITH DIARYLUREAS [J].
CURRAN, DP ;
KUO, LH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3259-3261
[8]  
Dessole G., 2004, SYNLETT, P2374
[9]   HYDROGEN-BOND DIRECTED COCRYSTALLIZATION AND MOLECULAR RECOGNITION PROPERTIES OF DIARYLUREAS [J].
ETTER, MC ;
URBANCZYKLIPKOWSKA, Z ;
ZIAEBRAHIMI, M ;
PANUNTO, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8415-8426
[10]   1,3-BIS(M-NITROPHENYL)UREA - AN EXCEPTIONALLY GOOD COMPLEXING AGENT FOR PROTON ACCEPTORS [J].
ETTER, MC ;
PANUNTO, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5896-5897