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

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 39期

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

页码：7037 / 7042

页数：6

共 45 条

[21] Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: Inversion of configuration at C9 dramatically improves catalyst performance [J].

McCooey, SH ;

Connon, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (39) :6367-6370

[22] THE NITROETHYLATION OF INDOLES .3. A SYNTHETIC ROUTE TO SUBSTITUTED TRYPTAMINES [J].

NOLAND, WE ;

LANGE, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (05) :1203-1209

[23] Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea [J].

Okino, T ;

Hoashi, Y ;

Furukawa, T ;

Xu, XN ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :119-125

[24] Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts [J].

Okino, T ;

Hoashi, Y ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12672-12673

[25] Thiourea-catalyzed nucleophilic addition of TMSCN and ketene silyl acetals to nitrones and aldehydes [J].

Okino, T ;

Hoashi, Y ;

Takemoto, Y .

TETRAHEDRON LETTERS, 2003, 44 (14) :2817-2821

[26]

Olah G. A., 1973, FRIEDEL CRAFTS CHEM

[27] Highly enantioselective Friedel-Crafts alkylations of pyrroles and indoles with α-hydroxy enones under Cu(II)-simple bis(oxazoline) catalysis [J].

Palomo, C ;

Oiarbide, M ;

Kardak, BG ;

García, JM ;

Linden, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4154-4155

[28] New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation [J].

Paras, NA ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4370-4371

[29] Activation of carbonyl compounds by double hydrogen bonding: An emerging tool in asymmetric catalysis [J].

Pihko, PM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (16) :2062-2064

[30] Metal-free organocatalysis through explicit hydrogen bonding interactions [J].

Schreiner, PR .

CHEMICAL SOCIETY REVIEWS, 2003, 32 (05) :289-296

← 1 2 3 4 5 →