Asymmetric Friedel-crafts alkylations of indoles with nitroalkenes catalyzed by Zn(II)-bisoxazoline complexes

被引：204

作者：

Jia, YX

Zhu, SF

Yang, Y

Zhou, QL ^{[1
]}

机构：

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

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 01期

关键词：

D O I：

10.1021/jo0516537

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel asymmetric Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by Zn(II)bisoxazoline complexes has been developed. The nitroalkylated indoles are synthesized in excellent yields and high enantioselectivities (up to 90% ee). The effects of ligand structure, metal salt, and solvent on the reaction are discussed. The substrates of the reaction can be aromatic, heteroaromatic, and even aliphatic nitroalkenes. The high reactivity and selectivity of the reaction are presumptively attributed to the activation and asymmetric induction of chiral Lewis acids coordinated by nitroalkene substrates through a 1,3-metal bonding model.

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页码：75 / 80

页数：6

相关论文

共 45 条

[1] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].

Alam, MM ;

Varala, R ;

Adapa, SR .

TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119

[2] Enantioselective copper-catalyzed conjugate addition of dialkyl zinc to nitro-olefins [J].

Alexakis, A ;

Benhaim, C .

ORGANIC LETTERS, 2000, 2 (17) :2579-2581

[3] 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

[4] Designing new α,β-unsaturated thioesters for the catalytic, enantioselective Friedel-Crafts alkylation of indoles [J].

Bandini, M ;

Melloni, A ;

Tommasi, S ;

Umani-Ronchi, A .

HELVETICA CHIMICA ACTA, 2003, 86 (11) :3753-3763

[5] 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

[6] A practical indium tribromide catalysed addition of indoles to nitroalkenes in aqueous media [J].

Bandini, M ;

Melchiorre, P ;

Melloni, A ;

Umani-ronchi, A .

SYNTHESIS-STUTTGART, 2002, (08) :1110-1114

[7] Efficient preparation of 2-indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile Michael acceptors:: New practical linear approach to alkyl 9H-β-Carboline-4-carboxylate [J].

Bartoli, G ;

Bosco, M ;

Giuli, S ;

Giuliani, A ;

Lucarelli, L ;

Marcantoni, E ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1941-1944

[8]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[9] ASYMMETRIC MICHAEL-ADDITIONS - STEREOSELECTIVE ALKYLATION OF CHIRAL, NON-RACEMIC ENOLATES BY NITROOLEFINS - PREPARATION OF ENANTIOMERICALLY PURE GAMMA-AMINOBUTYRIC AND SUCCINIC ACID-DERIVATIVES [J].

CALDERARI, G ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1985, 68 (06) :1592-1604

[10] Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes [J].

Choi, H ;

Hua, ZH ;

Ojima, I .

ORGANIC LETTERS, 2004, 6 (16) :2689-2691

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