Malonate-type bis(oxazoline) ligands with sp2 hybridized bridge carbon: synthesis and application in Friedel-Crafts alkylation and allylic alkylation

被引：21

作者：

Chen, Hongliang ^{[1
]}

Du, Fengpei ^{[1
]}

Liu, Lei ^{[1
]}

Li, Jing ^{[1
]}

Zhao, Qiuying ^{[1
]}

Fu, Bin ^{[1
]}

机构：

[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 49期

关键词：

Bis(oxazoline); Asymmetric catalysis; Friedel-Crafts; Allylic alkylation; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; OXAZOLINE-CONTAINING LIGANDS; ASYMMETRIC MICHAEL ADDITION; DIELS-ALDER REACTIONS; SUBSTITUTION-REACTIONS; COPPER(II) COMPLEXES; CHIRAL LIGANDS; BIS-OXAZOLINE; BITE-ANGLE; ARYLID-BOX;

D O I：

10.1016/j.tet.2011.09.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

A series of simple and new C-2-symmetric diphenylmethylidene malonate-type bis(oxazoline) ligands were synthesized and applied to the Friedel-Crafts reaction and allylic alkylation. The Cu(II) complex of ligand 4b bearing the benzyl group afforded good to excellent enantioselectivity for the F-C adducts (up to >99% ee) between indole and alkylidene malonate, and the palladium complex of ligand 4c bearing the phenyl group afforded excellent enantioselectivity (up to 94% ee) for the allylic allcylation product. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：9602 / 9608

页数：7

共 61 条

[1]

New dihydroxy bis(oxazoline) ligands for the palladium-catalyzed asymmetric allylic alkylation:: Experimental investigations of the origin of the reversal of the enantioselectivity [J].

Aït-Haddou, H ;

Hoarau, O ;

Cramailére, D ;

Pezet, F ;

Daran, JC ;

Balavoine, GGA .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (03) :699-707

[2]

[Anonymous], 2009, Angew. Chem. Int. Ed

[3]

Applications of enantiopure 4,5-diphenyl substituted box and pybox ligands in asymmetric catalysis [J].

Bayardon, J ;

Sinou, D ;

Guala, M ;

Desimoni, G .

TETRAHEDRON-ASYMMETRY, 2004, 15 (20) :3195-3200

[4]

Enantiopure fluorous bis(oxazolines): Synthesis and applications in catalytic asymmetric reactions [J].

Bayardon, J ;

Sinou, D .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3121-3128

[5]

Molybdenum-catalyzed asymmetric allylic alkylations [J].

Belda, O ;

Moberg, C .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (03) :159-167

[6]

Cu(I) catalysed cyclopropanation of olefins: Stereoselectivity studies with arylid-box and isbut-box ligands [J].

Burke, Anthony J. ;

da Palma Carreiro, Elisabete ;

Chercheja, Serghei ;

Moura, Nuno M. M. ;

Ramalho, J. P. Prates ;

Rodrigues, Ana Isabel ;

dos Santos, Carla I. M. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (22) :4863-4874

[7]

Isbut-Box:: A new chiral C2 symmetric bis-oxazoline for catalytic enantioselective synthesis [J].

Carreiro, ED ;

Chercheja, S ;

Burke, AJ ;

Ramalho, JPP ;

Rodrigues, AI .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 236 (1-2) :38-45

[8]

Arylid-Box: A new family of chiral bis-oxazoline ligands for metal mediated catalytic enantioselective synthesis [J].

Carreiro, Elisabete da Palma ;

Chercheja, Serghei ;

Moura, Nuno M. M. ;

Gertrudes, Claudia S. C. ;

Burke, Anthony J. .

INORGANIC CHEMISTRY COMMUNICATIONS, 2006, 9 (08) :823-826

[9]

Synthesis of highly modular bis(oxazoline) ligands by Suzuki cross-coupling and evaluation as catalytic ligands [J].

Cattoen, Xavier ;

Pericas, Miquel A. .

TETRAHEDRON, 2009, 65 (39) :8199-8205

[10]

DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].

COREY, EJ ;

IMAI, N ;

ZHANG, HY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729

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