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Volumn 24, Issue 12, 2012, Pages 1092-1095

Noncovalent immobilization of ionic-tagged box-Cu(OAc)2 complex and its application in asymmetric henry reaction

Author keywords

asymmetric Henry reaction; bis(oxazolines); hydrogen bonding; immobilization; SBA 15

Indexed keywords

2 METHOXYBENZALDEHYDE; 2 PROPANOL; BENZALDEHYDE DERIVATIVE; COPPER DERIVATIVE; OXAZOLINE DERIVATIVE; SILICON DIOXIDE; UNCLASSIFIED DRUG;

EID: 84870444570     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22104     Document Type: Article
Times cited : (13)

References (35)
  • 1
    • 65249154043 scopus 로고    scopus 로고
    • Noncovalent immobilization of enantioselective catalysts
    • Fraile J, García J, Mayoral J,. Noncovalent immobilization of enantioselective catalysts. Chem Rev 2009; 109: 360-417.
    • (2009) Chem Rev , vol.109 , pp. 360-417
    • Fraile, J.1    García, J.2    Mayoral, J.3
  • 3
    • 0033618082 scopus 로고    scopus 로고
    • Preparation, characterization, and performance of tripodal polyphosphine rhodium catalysts immobilized on silica via hydrogen bonding
    • Bianchini C, Burnaby D, Evans J, Frediani P, Meli A, Oberhauser W, Psaro R, Sordelli L, Vizza F,. Preparation, characterization, and performance of tripodal polyphosphine rhodium catalysts immobilized on silica via hydrogen bonding. J Am Chem Soc 1999; 121: 5961-5971.
    • (1999) J Am Chem Soc , vol.121 , pp. 5961-5971
    • Bianchini, C.1    Burnaby, D.2    Evans, J.3    Frediani, P.4    Meli, A.5    Oberhauser, W.6    Psaro, R.7    Sordelli, L.8    Vizza, F.9
  • 4
    • 47249121361 scopus 로고    scopus 로고
    • Benzene hydrogenation by silica-supported catalysts made of palladium nanoparticles and electrostatically immobilized rhodium single sites
    • Barbaro P, Bianchini C, Santo V, Meli A, Moneti S, Pirovano C, Psaro R, Sordelli L, Vizza F,. Benzene hydrogenation by silica-supported catalysts made of palladium nanoparticles and electrostatically immobilized rhodium single sites. Organometallics 2008; 27: 2809-2824.
    • (2008) Organometallics , vol.27 , pp. 2809-2824
    • Barbaro, P.1    Bianchini, C.2    Santo, V.3    Meli, A.4    Moneti, S.5    Pirovano, C.6    Psaro, R.7    Sordelli, L.8    Vizza, F.9
  • 6
    • 0034699480 scopus 로고    scopus 로고
    • Non-covalent immobilization of homogeneous cationic chiral rhodium-phosphine catalysts on silica surfaces
    • Rege F, Morita D, Ott K, Tumas W, Broene R,. Non-covalent immobilization of homogeneous cationic chiral rhodium-phosphine catalysts on silica surfaces. Chem Commun 2000;18: 1797-1798.
    • (2000) Chem Commun , vol.18 , pp. 1797-1798
    • Rege, F.1    Morita, D.2    Ott, K.3    Tumas, W.4    Broene, R.5
  • 7
    • 64549090213 scopus 로고    scopus 로고
    • Supramolecular chiral dendritic monophosphites assembled by hydrogen bonding and their use in the Rh-catalyzed asymmetric hydrogenation
    • Li Y, He Y, Li Z, Zhang F, Fan Q,. Supramolecular chiral dendritic monophosphites assembled by hydrogen bonding and their use in the Rh-catalyzed asymmetric hydrogenation. Org Biomol Chem 2009; 7: 1890-1895.
    • (2009) Org Biomol Chem , vol.7 , pp. 1890-1895
    • Li, Y.1    He, Y.2    Li, Z.3    Zhang, F.4    Fan, Q.5
  • 9
    • 0038384661 scopus 로고    scopus 로고
    • Application of immobilized rhodium catalyst precursors in enantio- and chemoselective hydrogenation reactions
    • Brandts J, Berben P,. Application of immobilized rhodium catalyst precursors in enantio- and chemoselective hydrogenation reactions. Org Process Res Dev 2003; 7: 393-398.
    • (2003) Org Process Res Dev , vol.7 , pp. 393-398
    • Brandts, J.1    Berben, P.2
  • 10
    • 85008090337 scopus 로고
    • Bis(oxazolines) as chiral ligands in metal-catalyzed asymmetric reactions. Catalytic, asymmetric cyclopropanation of olefins
    • Evans D, Woerpel K, Hinman M, Faul M,. Bis(oxazolines) as chiral ligands in metal-catalyzed asymmetric reactions. Catalytic, asymmetric cyclopropanation of olefins. J Am Chem Soc 1991; 113: 726-728.
    • (1991) J Am Chem Soc , vol.113 , pp. 726-728
    • Evans, D.1    Woerpel, K.2    Hinman, M.3    Faul, M.4
  • 11
    • 39649122390 scopus 로고    scopus 로고
    • Metal-bis(oxazoline) complexes: From coordination chemistry to asymmetric catalysis
    • Rasappan R, Laventine D, Reiser O,. Metal-bis(oxazoline) complexes: from coordination chemistry to asymmetric catalysis. Coor Chem Rev 2008; 252: 702-714.
    • (2008) Coor Chem Rev , vol.252 , pp. 702-714
    • Rasappan, R.1    Laventine, D.2    Reiser, O.3
  • 12
    • 85022460851 scopus 로고
    • Designed catalyst for enantioselective Diels-Alder addition from a C2-symmetric chiral bis(oxazoline)-iron(III) complex
    • Corey E, Imai N, Zhang H,. Designed catalyst for enantioselective Diels-Alder addition from a C2-symmetric chiral bis(oxazoline)-iron(III) complex. J Am Chem Soc 1991; 113: 728-729.
    • (1991) J Am Chem Soc , vol.113 , pp. 728-729
    • Corey, E.1    Imai, N.2    Zhang, H.3
  • 13
    • 33745360917 scopus 로고    scopus 로고
    • Asymmetric cyclopropanation catalyzed by fluorous bis(oxazolines)-copper complexes
    • Bayardon J, Holczknecht O, Pozzi G, Sinou D,. Asymmetric cyclopropanation catalyzed by fluorous bis(oxazolines)-copper complexes. Tetrahedron: Asymmetry 2006; 17: 1568-1572.
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 1568-1572
    • Bayardon, J.1    Holczknecht, O.2    Pozzi, G.3    Sinou, D.4
  • 14
    • 38849147760 scopus 로고    scopus 로고
    • Efficient heterogeneous asymmetric catalysis of the Mukaiyama aldol reaction by silica- and ionic liquid-supported Lewis acid copper(II) complexes of bis(oxazolines)
    • Doherty S, Goodrich P, Hardacre C, PÖrvulescu V, Paun C,. Efficient heterogeneous asymmetric catalysis of the Mukaiyama aldol reaction by silica- and ionic liquid-supported Lewis acid copper(II) complexes of bis(oxazolines). Adv Synth Catal 2008; 350: 295-302.
    • (2008) Adv Synth Catal , vol.350 , pp. 295-302
    • Doherty, S.1    Goodrich, P.2    Hardacre, C.3    Pörvulescu, V.4    Paun, C.5
  • 15
    • 0034674549 scopus 로고    scopus 로고
    • 2-symmetric chiral bis(oxazoline)-lanthanide complexes
    • 2-symmetric chiral bis(oxazoline)-lanthanide complexes. Tetrahedron: Asymmetry 2000; 11: 2347-2357.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 2347-2357
    • Qian, C.T.1    Wang, L.2
  • 16
    • 77954029753 scopus 로고    scopus 로고
    • Preparation, structure and catalytic activity of copper(II) complexes of novel 4,4'-BOX ligands
    • Frain D, Kirby F, McArdle P, O'Leary P,. Preparation, structure and catalytic activity of copper(II) complexes of novel 4,4'-BOX ligands Tetrahedron Lett 2010; 51: 4103-4106.
    • (2010) Tetrahedron Lett , vol.51 , pp. 4103-4106
    • Frain, D.1    Kirby, F.2    McArdle, P.3    O'Leary, P.4
  • 17
    • 1642588252 scopus 로고    scopus 로고
    • Facile and rapid immobilization of copper(II) bis(oxazoline) catalysts on silica: Application to Diels-Alder reactions, recycling, and unexpected effects on enantioselectivity
    • O'Leary P, Krosveld N, De Jong K, Koten G, Gebbink R,. Facile and rapid immobilization of copper(II) bis(oxazoline) catalysts on silica: application to Diels-Alder reactions, recycling, and unexpected effects on enantioselectivity Tetrahedron Lett 2004; 45: 3177-3180.
    • (2004) Tetrahedron Lett , vol.45 , pp. 3177-3180
    • O'Leary, P.1    Krosveld, N.2    De Jong, K.3    Koten, G.4    Gebbink, R.5
  • 18
    • 34248647579 scopus 로고    scopus 로고
    • Electrostatic immobilisation of copper(I) and copper(II) bis(oxazolinyl)pyridine catalysts on silica: Application to the synthesis of propargylamines via direct addition of terminal alkynes to imines
    • McDonagh C, Conghaile P, Klein Gebbink R, O'Leary P,. Electrostatic immobilisation of copper(I) and copper(II) bis(oxazolinyl)pyridine catalysts on silica: application to the synthesis of propargylamines via direct addition of terminal alkynes to imines. Tetrahedron Lett 2007; 48: 4387-4390.
    • (2007) Tetrahedron Lett , vol.48 , pp. 4387-4390
    • McDonagh, C.1    Conghaile, P.2    Klein Gebbink, R.3    O'Leary, P.4
  • 19
    • 29144507739 scopus 로고    scopus 로고
    • Asymmetric Diels-Alder reactions with hydrogen bonding heterogeneous catalysts and mechanistic studies on the reversal of enantioselectivity
    • Wang H, Liu X, Xia H, Liu P, Gao J, Ying P, Xiao J, Li C,. Asymmetric Diels-Alder reactions with hydrogen bonding heterogeneous catalysts and mechanistic studies on the reversal of enantioselectivity Tetrahedron 2006; 62: 1025-1032.
    • (2006) Tetrahedron , vol.62 , pp. 1025-1032
    • Wang, H.1    Liu, X.2    Xia, H.3    Liu, P.4    Gao, J.5    Ying, P.6    Xiao, J.7    Li, C.8
  • 20
    • 84945959007 scopus 로고
    • Basic character of rare earth metal alkoxides. Utilization in catalytic carbon-carbon bond-forming reactions and catalytic asymmetric nitroaldol reactions
    • Sasai H, Suzuki T, Arai M, Arai T, Shibasaki M,. Basic character of rare earth metal alkoxides. Utilization in catalytic carbon-carbon bond-forming reactions and catalytic asymmetric nitroaldol reactions. J Am Chem Soc 1992; 114: 4418-4420.
    • (1992) J Am Chem Soc , vol.114 , pp. 4418-4420
    • Sasai, H.1    Suzuki, T.2    Arai, M.3    Arai, T.4    Shibasaki, M.5
  • 21
    • 0035804426 scopus 로고    scopus 로고
    • The Henry reaction: Recent examples
    • Luzzio F,. The Henry reaction: recent examples. Tetrahedron 2001; 57: 915-945.
    • (2001) Tetrahedron , vol.57 , pp. 915-945
    • Luzzio, F.1
  • 22
    • 84993914143 scopus 로고
    • Functionalized nitroalkanes as useful reagents for alkyl anion synthons
    • Rosini G, Ballini R,. Functionalized nitroalkanes as useful reagents for alkyl anion synthons. Synthesis 1988; 11: 833-847.
    • (1988) Synthesis , vol.11 , pp. 833-847
    • Rosini, G.1    Ballini, R.2
  • 23
    • 84857563163 scopus 로고    scopus 로고
    • Salicylaldimine based copper (II) complex-potential catalyst for asymmetric Henry reaction
    • Ananthi N, Balakrishnan U, Velmathi S,. Salicylaldimine based copper (II) complex-potential catalyst for asymmetric Henry reaction. Arkivoc 2010; 11: 370-379.
    • (2010) Arkivoc , vol.11 , pp. 370-379
    • Ananthi, N.1    Balakrishnan, U.2    Velmathi, S.3
  • 24
    • 79955437696 scopus 로고    scopus 로고
    • Asymmetric Henry reaction catalyzed by a chiral Cu(II) complex: A facile enantioselective synthesis of (S)-2-nitro-1-arylethanols
    • Reddy B, Reddy S, Manisha S, Madan C,. Asymmetric Henry reaction catalyzed by a chiral Cu(II) complex: a facile enantioselective synthesis of (S)-2-nitro-1-arylethanols. Tetrahedron: Asymmetry 2011; 22: 530-535.
    • (2011) Tetrahedron: Asymmetry , vol.22 , pp. 530-535
    • Reddy, B.1    Reddy, S.2    Manisha, S.3    Madan, C.4
  • 25
    • 0142040727 scopus 로고    scopus 로고
    • A New copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction
    • Evans D, Seidel D, Rueping M, Lam H, Shaw J, Downey C,. A New copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction. J Am Chem Soc 2003; 125: 12692-12693.
    • (2003) J Am Chem Soc , vol.125 , pp. 12692-12693
    • Evans, D.1    Seidel, D.2    Rueping, M.3    Lam, H.4    Shaw, J.5    Downey, C.6
  • 26
    • 68949163231 scopus 로고    scopus 로고
    • Combining fluorous and triazole moieties for the tagging of chiral azabis(oxazoline) ligands
    • Rasappan R, Olbrich T, Reisera O,. Combining fluorous and triazole moieties for the tagging of chiral azabis(oxazoline) ligands. Adv Synth Catal 2009; 351: 1961-1967.
    • (2009) Adv Synth Catal , vol.351 , pp. 1961-1967
    • Rasappan, R.1    Olbrich, T.2    Reisera, O.3
  • 27
    • 78650171639 scopus 로고    scopus 로고
    • Chiral Cu(II) complexes as recyclable catalysts for asymmetric nitroaldol (Henry) reaction in ionic liquids as greener reaction media
    • Khan N, Prasetyanto E, Kim Y, Ansari M, Park S,. Chiral Cu(II) complexes as recyclable catalysts for asymmetric nitroaldol (Henry) reaction in ionic liquids as greener reaction media. Catal Lett 2010; 140: 189-196.
    • (2010) Catal Lett , vol.140 , pp. 189-196
    • Khan, N.1    Prasetyanto, E.2    Kim, Y.3    Ansari, M.4    Park, S.5
  • 28
    • 79955911271 scopus 로고    scopus 로고
    • Charge-transfer interactions: An efficient tool for recycling bis(oxazoline)-copper complexes in asymmetric Henry reactions
    • Didier D, Magnier-Bouvier C, Schulza E,. Charge-transfer interactions: an efficient tool for recycling bis(oxazoline)-copper complexes in asymmetric Henry reactions. Adv Synth Catal 2011; 353: 1087-1095.
    • (2011) Adv Synth Catal , vol.353 , pp. 1087-1095
    • Didier, D.1    Magnier-Bouvier, C.2    Schulza, E.3
  • 29
    • 80053475393 scopus 로고    scopus 로고
    • Chiral cationic Pd-phosphinooxazolidine catalysts for a highly efficient asymmetric Diels-Alder reaction in ionic liquids
    • Hiroto N, Yasuhiro N, Kouichi T, Reiko F, Koji U, Mitsuhiro T,. Chiral cationic Pd-phosphinooxazolidine catalysts for a highly efficient asymmetric Diels-Alder reaction in ionic liquids. Heterocycles 2008; 76: 381-390.
    • (2008) Heterocycles , vol.76 , pp. 381-390
    • Hiroto, N.1    Yasuhiro, N.2    Kouichi, T.3    Reiko, F.4    Koji, U.5    Mitsuhiro, T.6
  • 30
    • 1342268953 scopus 로고    scopus 로고
    • Comparison of the immobilization of chiral bis(oxazoline)-copper complexes onto anionic solids and in ionic liquids
    • Fraile J, García J, Herrerías C, Mayoral J, Gmough S, Vaultier M,. Comparison of the immobilization of chiral bis(oxazoline)-copper complexes onto anionic solids and in ionic liquids. Green Chem 2004; 6: 93-98.
    • (2004) Green Chem , vol.6 , pp. 93-98
    • Fraile, J.1    García, J.2    Herrerías, C.3    Mayoral, J.4    Gmough, S.5    Vaultier, M.6
  • 32
    • 77956508782 scopus 로고    scopus 로고
    • Heterogeneous chiral copper complexes of amino alcohol for asymmetric nitroaldol reaction
    • Mayani V, Abdi S, Kureshy R, Khan N, Das A, Bajaj H,. Heterogeneous chiral copper complexes of amino alcohol for asymmetric nitroaldol reaction. J Org Chem 2010; 75: 6191-6195.
    • (2010) J Org Chem , vol.75 , pp. 6191-6195
    • Mayani, V.1    Abdi, S.2    Kureshy, R.3    Khan, N.4    Das, A.5    Bajaj, H.6
  • 33
    • 34250666228 scopus 로고    scopus 로고
    • Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation
    • Bandini M, Benaglia M, Sinisi R, Tommasi S, Umani-Ronchi A,. Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation. Org Lett 2007; 9: 2151-2153.
    • (2007) Org Lett , vol.9 , pp. 2151-2153
    • Bandini, M.1    Benaglia, M.2    Sinisi, R.3    Tommasi, S.4    Umani-Ronchi, A.5
  • 34
    • 77949307801 scopus 로고    scopus 로고
    • Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support
    • Lee J, Kim J, Shin Y, Yeom C, Lee J, Hyeon T, Kim B,. Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support. Tetrahedron: Asymmetry 2010; 21: 285-291.
    • (2010) Tetrahedron: Asymmetry , vol.21 , pp. 285-291
    • Lee, J.1    Kim, J.2    Shin, Y.3    Yeom, C.4    Lee, J.5    Hyeon, T.6    Kim, B.7
  • 35
    • 84862799790 scopus 로고    scopus 로고
    • Recyclable copper catalysts based on ionic-tagged C2-symmetric Indabox ligands and their application in asymmetric Henry reactions
    • 28-34
    • Li Z, Zhou Z, Hao X, Zhang J, Dong X, Liu Y, Sun W, Cao D,. Recyclable copper catalysts based on ionic-tagged C2-symmetric Indabox ligands and their application in asymmetric Henry reactions. Appl Catal A: Gen 2012; 425-426:28-34.
    • (2012) Appl Catal A: Gen , pp. 425-426
    • Li, Z.1    Zhou, Z.2    Hao, X.3    Zhang, J.4    Dong, X.5    Liu, Y.6    Sun, W.7    Cao, D.8


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