Catalytic enantioselective Friedel-Crafts alkylation at the 2-position of indole with simple enones

被引：43

作者：

Blay, Gonzalo ^{[1
]}

Fernandez, Isabel ^{[1
]}

Pedro, Jose R. ^{[1
]}

Vila, Carlos ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Spain

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 38期

关键词：

enantioselective catalysis; zirconium complexes; BINOL; heterocycles; dihydroindole; conjugate addition;

D O I：

10.1016/j.tetlet.2007.07.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A procedure for the enantioselective alkylation of indole at the 2-position with simple non-chelating enones is described for the first time. Reaction between 4,7-dihydroindole and enones in the presence of zirconium(IV)-BINOL complexes, followed by a p-benzoquinone oxidation gives indoles alkylated at the 2-position with good yields and moderate enantioselectivities. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6731 / 6734

页数：4

共 41 条

[1] TiCl4/t-BuNH2-promoted hydroamination/annulation of δ-keto-acetylenes:: Synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes [J].

Abbiati, Giorgio ;

Casoni, Alessandro ;

Canevari, Valentina ;

Nava, Donatella ;

Rossi, Elisabetta .

ORGANIC LETTERS, 2006, 8 (21) :4839-4842

[2] Highly enantioselective copper(I)-phosphoramidite-catalysed additions of organoaluminium reagents to enones [J].

Alexakis, A ;

Albrow, V ;

Biswas, K ;

d'Augustin, M ;

Prieto, O ;

Woodward, S .

CHEMICAL COMMUNICATIONS, 2005, (22) :2843-2845

[3] 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

[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] Can simple enones be useful partners for the catalytic stereoselective alkylation of indoles? [J].

Bandini, M ;

Fagioli, M ;

Garavelli, M ;

Melloni, A ;

Trigari, V ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) :7511-7518

[6] 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

[7] 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

[8] Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones [J].

Bartoli, Giuseppe ;

Bosco, Marcella ;

Carlone, Armando ;

Pesciaioli, Fabio ;

Sambri, Letizia ;

Melchiorre, Paolo .

ORGANIC LETTERS, 2007, 9 (07) :1403-1405

[9] Highly enantioselective Friedel-Crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes [J].

Blay, Gonzalo ;

Fernandez, Isabel ;

Pedro, Jose R. ;

Vila, Carlos .

ORGANIC LETTERS, 2007, 9 (13) :2601-2604

[10] Aziridin-2-yl methanols as organocatalysts in Diels-Alder reactions and Friedel-Crafts alkylations of N-methyl-pyrrole and N-methyl-indole [J].

Bonini, Bianca F. ;

Capito, Elena ;

Comes-Franchini, Mauro ;

Fochi, Mariafrancesca ;

Riccia, Alfredo ;

Zwanenburg, Binne .

TETRAHEDRON-ASYMMETRY, 2006, 17 (22) :3135-3143

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