InBr3-catalyzed friedel-crafts addition of indoles to chiral aromatic epoxides:: A facile route to enantiopure indolyl derivatives

被引：81

作者：

Bandini, M ^{[1
]}

Cozzi, PG ^{[1
]}

Melchiorre, P ^{[1
]}

Umani-Ronchi, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

D O I：

10.1021/jo0256235

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic optically active epoxides can be opened in a regioselective and clean way with indoles in the presence of catalytic amount of InBr3 (1 mol %). The reaction takes place with a S(N)2 pathway affording the 2-aryl-2-(3'-indolyl)-ethan-1-ols with excellent enantio selectivity (ee up to 99%).

引用

页码：5386 / 5389

页数：4

共 46 条

[11]

Fenniri H., 2000, COMBINATORIAL CHEM

[12] Organic chemistry on solid supports [J].

Fruchtel, JS ;

Jung, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42

[13] Catalytic enantioselective Friedel-Crafts reactions of aromatic compounds with glyoxylate: A simple procedure for the synthesis of optically active aromatic mandelic acid esters [J].

Gathergood, N ;

Zhuang, W ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (50) :12517-12522

[14]

GILCHRIST TL, 1988, HETEROCYCLIC CHEM, V25, P1

[15]

GLENNON RA, 1997, J MED CHEM, V40, P1

[16] On the mechanism of asymmetric nucleophilic ring-opening of epoxides catalyzed by (salen)Cr-III complexes [J].

Hansen, KB ;

Leighton, JL ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10924-10925

[17]

Hao J, 2001, SYNLETT, P1443

[18] Solid-phase organic reactions: A review of the recent literature [J].

Hermkens, PHH ;

Ottenheijm, HCJ ;

Rees, D .

TETRAHEDRON, 1996, 52 (13) :4527-4554

[19]

HESSE M, 1978, ALKALOID CHEM

[20] Asymmetric catalysis of the Friedel-Crafts reaction with fluoral by chiral binaphthol-derived titanium catalysts through asymmetric activation [J].

Ishii, A ;

Soloshonok, VA ;

Mikami, K .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1597-1599

← 1 2 3 4 5 →