Cu(II) homogeneous and heterogeneous catalysts for the asymmetric Henry reaction

被引：39

作者：

Jones, Matthew D. ^{[1
]}

Cooper, Christine J.

Mahon, Mary F. ^{[1
]}

Raithby, Paul R.

Apperley, David ^{[2
]}

Wolowska, Joanna ^{[3
]}

Collison, David ^{[3
]}

机构：

[1] Univ Bath, Dept Chem, Bath Chem Crystallog Unit, Bath BA2 7AY, Avon, England

[2] Univ Durham, Dept Chem, Solid State NMR Serv, Durham DH1 3LE, England

[3] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2010年 / 325卷 / 1-2期

基金：

英国工程与自然科学研究理事会;

关键词：

Homogeneous and heterogeneous catalysts; Copper; Supported catalysts; BOND-FORMING REACTIONS; COPPER(II) COMPLEXES; NITROALDOL REACTION; CRYSTAL-STRUCTURES; LIGANDS; EFFICIENT; TRANS-1,2-DIAMINOCYCLOHEXANE; BIS(OXAZOLINE); DERIVATIVES; DIAMINE;

D O I：

10.1016/j.molcata.2010.03.013

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

New Cu(II) complexes have been prepared and characterised via single crystal X-ray diffraction studies, EPR spectroscopy, elemental analysis and high resolution mass spectrometry. In all cases 1:2 (copper to ligand) stoichiometric complexes were isolated. The homogeneous Cu(II) complexes were tested for the asymmetric Henry reaction. Conversions in excess of 70% were obtained with enantioselectivities in the range 0-78%. Heterogeneous Cu(II) catalysts have been prepared. In these cases high conversions were obtained. However, after prolonged reaction time the main product observed was 1,3-dinitro-2-phenyl propane. The formation of this product can be curtailed by both decreasing the catalyst loading and employing shorter reaction times. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：8 / 14

页数：7

共 56 条

[1] Design of grafted copper complex in mesoporous silica in defined coordination, hydrophobicity and confinement states [J].

Abry, Sebastien ;

Thibon, Aurore ;

Albela, Belen ;

Delichere, Pierre ;

Banse, Frederic ;

Bonneviot, Laurent .

NEW JOURNAL OF CHEMISTRY, 2009, 33 (03) :484-496

[2] One pot synthesis of 3,5-alkylated acetophenone and methyl benzoate derivatives via an anionic domino process [J].

Ballini, R ;

Barboni, L ;

Fiorini, D ;

Giarlo, G ;

Palmieri, A .

CHEMICAL COMMUNICATIONS, 2005, (20) :2633-2634

[3] Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation [J].

Bandini, Marco ;

Benaglia, Maurizio ;

Sinisi, Riccardo ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

ORGANIC LETTERS, 2007, 9 (11) :2151-2153

[4] Highly enantioselective nitroaldol reaction catalyzed by new chiral copper complexes [J].

Bandini, Marco ;

Piccinelli, Fabio ;

Tommasi, Simona ;

Umani-Ronchi, Achille ;

Ventrici, Caterina .

CHEMICAL COMMUNICATIONS, 2007, (06) :616-618

[5] Straightforward preparation of highly enantioselective anchored chiral homogeneous catalysts [J].

Barnard, CFJ ;

Rouzaud, J ;

Stevenson, SH .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (02) :164-167

[6]

Becker M, 2000, EUR J INORG CHEM, P719

[7] Chiral lanthanum-lithium-binaphthol complex covalently bonded to silica and MCM-41 for enantio selective nitroaldol (Henry) reaction [J].

Bhatt, AP ;

Pathak, K ;

Jasra, RV ;

Kureshy, RI ;

Khan, NUH ;

Abdi, SHR .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 244 (1-2) :110-117

[8] A catalytic highly enantioselective direct synthesis of 2-bromo-2-nitroalkan-1-ols through a Henry reaction [J].

Blay, Gonzalo ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

CHEMICAL COMMUNICATIONS, 2008, (39) :4840-4842

[9] New highly asymmetric henry reaction catalyzed by CuII and a C1-Symmetric aminopyridine ligand, and its application to the synthesis of miconazole [J].

Blay, Gonzalo ;

Domingo, Luis R. ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (15) :4725-4730

[10] Enantioselective Henry reaction catalyzed with copper(II)-iminopyridine complexes [J].

Blay, Gonzalo ;

Climent, Estela ;

Fernandez, Isabel ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (13) :1603-1612

← 1 2 3 4 5 6 →