Asymmetric Friedel-Crafts addition of indoles to N-sulfonyl aldimines:: A simple approach to optically active 3-indolyl-methanamine derivatives

被引：149

作者：

Jia, YX

Xie, JH

Duan, HF

Wang, LX

Zhou, QL ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 08期

关键词：

D O I：

10.1021/ol0602001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective copper(II)-catalyzed Friedel-Crafts addition of indoles to N-sulfonyl aldimines was developed using chiral bisoxazoline as ligands, and high enantioselectivities (up to 96% ee) were achieved.

引用

页码：1621 / 1624

页数：4

共 26 条

[1] Kinetic resolution of epoxides by a C-C bond-forming reaction:: Highly enantioselective addition of indoles to cis, trans, and meso aromatic epoxides catalyzed by [Cr(salen)] complexes [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :84-87

[2] 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

[3] ENANTIOSELECTIVE CATALYSIS WITH A NEW ZIRCONIUM TRICHLORIDE LEWIS ACID CONTAINING A DIBORNACYCLOPENTADIENYL LIGAND [J].

ERKER, G ;

VANDERZEIJDEN, AAH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05) :512-514

[4] A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines:: Synthesis of unsymmetrical diaryl amines and triaryl methanes [J].

Esquivias, J ;

Arrayás, RG ;

Carretero, JC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (04) :629-633

[5] Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].

Evans, DA ;

Scheidt, KA ;

Fandrick, KR ;

Lam, HW ;

Wu, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10780-10781

[6] Enantioselective Friedel-Crafts alkylations of α-β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].

Evans, DA ;

Fandrick, KR ;

Song, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8942-8943

[7] 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

[8] 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

[9]

Jensen KB, 2001, ANGEW CHEM INT EDIT, V40, P160, DOI 10.1002/1521-3773(20010105)40:1<160::AID-ANIE160>3.0.CO

[10]

2-S

← 1 2 3 →