메뉴 건너뛰기
Catalysis Letters
Volumn 140, Issue 3-4, 2010, Pages 189-196
Chiral Cu(II) complexes as recyclable catalysts for asymmetric nitroaldol (Henry) reaction in ionic liquids as greener reaction media
Author keywords

Asymmetric nitroaldol reaction; Chiral catalysis; Cu(II) complex; Ionic liquid; Recyclable
Indexed keywords

CHIRAL CATALYSIS; COPPER ACETATES; CU COMPLEXES; ENANTIOSELECTIVE; ENVIRONMENTALLY BENIGN; HIGH ENANTIOSELECTIVITY; IN-SITU; NITROALCOHOLS; NITROALDOL; NITROMETHANE; REACTION MEDIA; REACTION MEDIUM; RECYCLABLE; RECYCLABLE CATALYST;
EID: 78650171639     PISSN: 1011372X     EISSN: 1572879X     Source Type: Journal    
DOI: 10.1007/s10562-010-0443-8     Document Type: Article
Times cited : (31)
References (75)
  • 2
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen EN, Pfaltz A, Yamamoto H (eds) Springer, Berlin
    • Shibasaki M, Gröger H (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis, vol III. Springer, Berlin
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Shibasaki M, G.1
  • 5
    • 0030577484 scopus 로고    scopus 로고
    • Catalytic asymmetric nitroaldol reaction of α,α-difluoro aldehydes mediated by rare earth-lithium-BINOL complexes
    • DOI 10.1016/S0040-4039(96)02090-4, PII S0040403996021338
    • K Iseki S Oishi H Sasai M Shibasaki 1996 Tetrahedron Lett 37 9081 1:CAS:528:DyaK2sXhtVCrsg%3D%3D 10.1016/S0040-4039(96)02090-4 (Pubitemid 26400470)
    • (1996) Tetrahedron Letters , vol.37 , Issue.50 , pp. 9081-9084
    • Iseki, K.1    Oishi, S.2    Sasai, H.3    Shibasaki, M.4
  • 7
    • 0027993912 scopus 로고
    • Diastereoselective catalytic asymmetric nitroaldol reaction utilizing rare earth-Li-(R)-BINOL complex. A highly efficient synthesis of norstatine
    • DOI 10.1016/0040-4039(94)88093-X
    • H Sasai W Kim T Suzuki M Shibasaki 1994 Tetrahedron Lett 35 6123 1:CAS:528:DyaK2MXlsVSjsg%3D%3D 10.1016/0040-4039(94)88093-X (Pubitemid 24256054)
    • (1994) Tetrahedron Letters , vol.35 , Issue.33 , pp. 6123-6126
    • Sasai, H.1    Kim, W.-S.2    Suzuki, T.3    Shibasaki, M.4    Mitsuda, M.5    Hasegawa, J.6    Ohashi, T.7
  • 8
    • 0030788730 scopus 로고    scopus 로고
    • 3tris((R)-binaphthoxide) complex ((R)-LnLB) (Ln: Lanthanoid)
    • DOI 10.1016/S0040-4039(97)01341-5, PII S0040403997013415
    • H Sasai M Hiroi YMA Yamada M Shibasaki 1997 Tetrahedron Lett 38 6031 1:CAS:528:DyaK2sXls1Ghu7k%3D 10.1016/S0040-4039(97)01341-5 (Pubitemid 27346489)
    • (1997) Tetrahedron Letters , vol.38 , Issue.34 , pp. 6031-6034
    • Sasai, H.1    Hiroi, M.2    Yamada, Y.M.A.3    Shibasaki, M.4
  • 9
    • 0000679569 scopus 로고    scopus 로고
    • 1:CAS:528:DyaK28Xjt1Kjs7g%3D 10.1351/pac199668030523
    • M Shibasaki H Sasai 1996 Pure Appl Chem 68 523 1:CAS:528: DyaK28Xjt1Kjs7g%3D 10.1351/pac199668030523
    • (1996) Pure Appl Chem , vol.68 , pp. 523
    • Shibasaki, M.1    Sasai, H.2
  • 10
  • 11
    • 0036625219 scopus 로고    scopus 로고
    • Lanthanide complexes in multifunctional asymmetric catalysis
    • DOI 10.1021/cr010297z
    • M Shibasaki N Yoshikawa 2002 Chem Rev 102 2187 1:CAS:528: DC%2BD38XjvFagsL4%3D 10.1021/cr010297z (Pubitemid 35377642)
    • (2002) Chemical Reviews , vol.102 , Issue.6 , pp. 2187-2209
    • Shibasaki, M.1    Yoshikawa, N.2
  • 12
    • 0036495323 scopus 로고    scopus 로고
    • A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction
    • DOI 10.1002/1521-3773(20020301)41:5<861::AID-ANIE861>3.0.CO;2-V
    • BM Trost VSC Yeh 2002 Angew Chem Int Ed 41 861 1:CAS:528: DC%2BD38XisVahsbg%3D 10.1002/1521-3773(20020301)41:5<861::AID-ANIE861>3.0. CO;2-V (Pubitemid 34218548)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.5 , pp. 861-863
    • Trost, B.M.1    Yeh, V.S.C.2
  • 16
    • 36148967632 scopus 로고    scopus 로고
    • Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media
    • DOI 10.1039/b712470h
    • SU Pandya RS Dickins D Parker 2007 Org Biomol Chem 5 3842 1:CAS:528:DC%2BD2sXhtlSmur7E 10.1039/b712470h (Pubitemid 350115427)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.23 , pp. 3842-3846
    • Pandya, S.U.1    Dickins, R.S.2    Parker, D.3
  • 21
    • 1442277240 scopus 로고    scopus 로고
    • New β-amino alcohols with a bicyclo[3.3.0]octane scaffold in an asymmetric Henry reaction
    • DOI 10.1016/j.tetasy.2003.11.040
    • Y Zhong P Tian G Lin 2004 Tetrahedron Asymmetr 15 771 1:CAS:528:DC%2BD2cXhslWjs7o%3D 10.1016/j.tetasy.2003.11.040 (Pubitemid 38270315)
    • (2004) Tetrahedron Asymmetry , vol.15 , Issue.5 , pp. 771-776
    • Zhong, Y.-W.1    Tian, P.2    Lin, G.-Q.3
  • 22
    • 0037078385 scopus 로고    scopus 로고
    • Activation of nitroaldol reactions by diethylzinc and amino alcohols or diamines as promoters
    • DOI 10.1016/S0040-4039(02)01768-9, PII S0040403902017689
    • G Klein S Pandiaraju O Reiser 2002 Tetrahedron Lett 43 7503 1:CAS:528:DC%2BD38XnsVWlurc%3D 10.1016/S0040-4039(02)01768-9 (Pubitemid 35283978)
    • (2002) Tetrahedron Letters , vol.43 , Issue.42 , pp. 7503-7506
    • Klein, G.1    Pandiaraju, S.2    Reiser, O.3
  • 23
    • 17744381382 scopus 로고    scopus 로고
    • 2-symmetric tridentate bis(oxazoline) and bis(thiazoline) complexes: Metal-controlled reversal of enantioselectivity
    • DOI 10.1021/jo050097d
    • D Du S Lu T Fang J Xu 2005 J Org Chem 70 3712 1:CAS:528: DC%2BD2MXis1ensbw%3D 10.1021/jo050097d (Pubitemid 40577584)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.9 , pp. 3712-3715
    • Du, D.-M.1    Lu, S.-F.2    Fang, T.3    Xu, J.4
  • 24
    • 33747771676 scopus 로고    scopus 로고
    • Modular iminopyridine ligands. Application to the enantioselective copper(II)-catalyzed Henry reaction
    • DOI 10.1016/j.tetasy.2006.07.025, PII S0957416606005180
    • G Blay E Climent I Fernández V Hernández-Olmos JR Pedro 2006 Tetrahedron Asymmetr 17 2046 1:CAS:528:DC%2BD28XoslCmsr0%3D 10.1016/j.tetasy.2006.07.025 (Pubitemid 44279970)
    • (2006) Tetrahedron Asymmetry , vol.17 , Issue.14 , pp. 2046-2049
    • Blay, G.1    Climent, E.2    Fernandez, I.3    Hernandez-Olmos, V.4    Pedro, J.R.5
  • 25
    • 46849091451 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1cXkt1Wkur0%3D 10.1021/ol800442s
    • S Liu C Wolf 2008 Org Lett 10 1831 1:CAS:528:DC%2BD1cXkt1Wkur0%3D 10.1021/ol800442s
    • (2008) Org Lett , vol.10 , pp. 1831
    • Liu, S.1    Wolf, C.2
  • 26
    • 72849133517 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXhsVeis7jE 10.1021/ol902380z
    • HY Kim K Oh 2009 Org Lett 11 5682 1:CAS:528:DC%2BD1MXhsVeis7jE 10.1021/ol902380z
    • (2009) Org Lett , vol.11 , pp. 5682
    • Kim, H.Y.1    Oh, K.2
  • 27
    • 70349907587 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXhtFajsr7N 10.1021/ol9018612
    • KY Spangler C Wolf 2009 Org Lett 11 4724 1:CAS:528:DC%2BD1MXhtFajsr7N 10.1021/ol9018612
    • (2009) Org Lett , vol.11 , pp. 4724
    • Spangler, K.Y.1    Wolf, C.2
  • 28
    • 0037020417 scopus 로고    scopus 로고
    • 3{tris(binaphthoxide)}] single catalyst component: Catalyst tuning with achiral additives
    • DOI 10.1002/1521-3773(20021004)41:19<3636::AID-ANIE3636>3.0.CO;2-B
    • J Tian N Yamagiwa S Matsunaga M Shibasaki 2002 Angew Chem Int Ed 41 3636 1:CAS:528:DC%2BD38XotFyms70%3D 10.1002/1521-3773(20021004)41:19<3636::AID- ANIE3636>3.0.CO;2-B (Pubitemid 35190471)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.19 , pp. 3636-3638
    • Tian, J.1    Yamagiwa, N.2    Matsunaga, S.3    Shibasaki, M.4
  • 31
    • 52449112922 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1cXpvVaku7Y%3D 10.1021/jo8010073
    • A Bulut A Aslan O Dogan 2008 J Org Chem 73 7373 1:CAS:528: DC%2BD1cXpvVaku7Y%3D 10.1021/jo8010073
    • (2008) J Org Chem , vol.73 , pp. 7373
    • Bulut, A.1    Aslan, A.2    Dogan, O.3
  • 32
    • 7444242815 scopus 로고    scopus 로고
    • 2-symmetric tridentate bis(thiazoline) and bis(oxazoline) ligands and their application in the enantioselective Henry reaction
    • DOI 10.1016/j.tetasy.2004.09.011, PII S0957416604007128
    • S Lu D Du S Zhang J Xu 2004 Tetrahedron Asymmetr 15 3433 1:CAS:528:DC%2BD2cXpt1SqsLw%3D 10.1016/j.tetasy.2004.09.011 (Pubitemid 39446788)
    • (2004) Tetrahedron Asymmetry , vol.15 , Issue.21 , pp. 3433-3441
    • Lu, S.-F.1    Du, D.-M.2    Zhang, S.-W.3    Xu, J.4
  • 34
    • 34250632623 scopus 로고    scopus 로고
    • Rational design of sterically and electronically easily tunable chiral bisimidazolines and their applications in dual lewis acid/brensted base catalysis for highly enantioselective nitroaldol (Henry) reactions
    • DOI 10.1002/chem.200601220
    • K Ma J You 2007 Chem Eur J 13 1863 1:CAS:528:DC%2BD2sXitlartbo%3D 10.1002/chem.200601220 (Pubitemid 46941942)
    • (2007) Chemistry - A European Journal , vol.13 , Issue.6 , pp. 1863-1871
    • Ma, K.1    You, J.2
  • 37
    • 34447109358 scopus 로고    scopus 로고
    • Development of new chiral phosphine-salen type ligands and their application in the Cu(I)-catalyzed enantioselective Henry reaction
    • DOI 10.1016/j.tetasy.2007.06.011, PII S0957416607004338
    • J-J Jianga M Shi 2007 Tetrahedron Asymmetr 18 1376 10.1016/j.tetasy.2007. 06.011 (Pubitemid 47030904)
    • (2007) Tetrahedron Asymmetry , vol.18 , Issue.11 , pp. 1376-1382
    • Jiang, J.-J.1    Shi, M.2
  • 38
    • 68349097408 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXltlCjtr8%3D 10.1002/chir.20661
    • J Guo J Mao 2009 Chirality 21 619 1:CAS:528:DC%2BD1MXltlCjtr8%3D 10.1002/chir.20661
    • (2009) Chirality , vol.21 , pp. 619
    • Guo, J.1    Mao, J.2
  • 41
    • 34249894998 scopus 로고    scopus 로고
    • Synthesis of novel chiral Schiff-base ligands and their application in asymmetric nitro aldol (Henry) reaction
    • DOI 10.1016/j.tetasy.2007.04.025, PII S0957416607003345
    • M Çolak T Aral H Hosgoren N Demirel 2007 Tetrahedron Asymmetr 18 1129 10.1016/j.tetasy.2007.04.025 (Pubitemid 46874052)
    • (2007) Tetrahedron Asymmetry , vol.18 , Issue.9 , pp. 1129-1133
    • Colak, M.1    Aral, T.2    Hosgoren, H.3    Demirel, N.4
  • 42
    • 39549087425 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1cXislGlsb4%3D 10.1016/j.ica.2007.08.003
    • Y Zhang L Xiang Q Wang X Duan G Zi 2008 Inorg Chim Acta 361 1246 1:CAS:528:DC%2BD1cXislGlsb4%3D 10.1016/j.ica.2007.08.003
    • (2008) Inorg Chim Acta , vol.361 , pp. 1246
    • Zhang, Y.1    Xiang, L.2    Wang, Q.3    Duan, X.4    Zi, G.5
  • 43
  • 44
    • 34748848573 scopus 로고    scopus 로고
    • Investigation of pore-size effects on base catalysis using amino-functionalized monodispersed mesoporous silica spheres as a model catalyst
    • DOI 10.1016/j.jcat.2007.08.010, PII S0021951707003235
    • TM Suzuki M Yamamoto K Fukumoto Y Akimoto K Yano 2007 J Catal 251 249 1:CAS:528:DC%2BD2sXhtFersLnF 10.1016/j.jcat.2007.08.010 (Pubitemid 47488318)
    • (2007) Journal of Catalysis , vol.251 , Issue.2 , pp. 249-257
    • Suzuki, T.M.1    Yamamoto, M.2    Fukumoto, K.3    Akimoto, Y.4    Yano, K.5
  • 45
    • 36148983364 scopus 로고    scopus 로고
    • Asymmetric nitroaldol reaction catalyzed by a chromium(III)-salen system
    • DOI 10.1016/j.tetasy.2007.10.023, PII S095741660700780X
    • R Kowalczyk Ł Sidorowicz J Skarzewski 2007 Tetrahedron Asymmetr 18 2581 1:CAS:528:DC%2BD2sXhtlKrsr7K 10.1016/j.tetasy.2007.10.023 (Pubitemid 350116579)
    • (2007) Tetrahedron Asymmetry , vol.18 , Issue.21 , pp. 2581-2586
    • Kowalczyk, R.1    Sidorowicz, L.2    Skarzewski, J.3
  • 46
    • 33846457382 scopus 로고    scopus 로고
    • A new copper (I)-tetrahydrosalen-catab zed asymmetric henry reaction and its extension to the synthesis of (S)-norphenylephrine
    • DOI 10.1002/chem.200601262
    • Y Xiong F Wang X Huang Y Wen X Feng 2007 Chem Eur J 13 829 1:CAS:528:DC%2BD2sXhtVOntrk%3D 10.1002/chem.200601262 (Pubitemid 46144558)
    • (2007) Chemistry - A European Journal , vol.13 , Issue.3 , pp. 829-833
    • Xiong, Y.1    Wang, F.2    Huang, X.3    Wen, Y.4    Feng, X.5
  • 47
    • 34249002709 scopus 로고    scopus 로고
    • Novel thiolated amino-alcohols as chiral ligands for copper-catalyzed asymmetric nitro-aldol reactions
    • DOI 10.1016/j.tetlet.2007.04.072, PII S0040403907007472
    • W Mansawat I Saengswang P U-prasitwong W Bhanthumnavin T Vilaivan 2007 Tetrahedron Lett 48 4235 1:CAS:528:DC%2BD2sXlsFKhtLY%3D 10.1016/j.tetlet.2007. 04.072 (Pubitemid 46778745)
    • (2007) Tetrahedron Letters , vol.48 , Issue.24 , pp. 4235-4238
    • Mansawat, W.1    Saengswang, I.2    U-prasitwong, P.3    Bhanthumnavin, W.4    Vilaivan, T.5
  • 50
    • 49049109227 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1cXhtVWksrnL 10.1016/j.tetasy.2008.06.036
    • G Lai S Wang Z Wang 2008 Tetrahedron Asymmetr 19 1813 1:CAS:528:DC%2BD1cXhtVWksrnL 10.1016/j.tetasy.2008.06.036
    • (2008) Tetrahedron Asymmetr , vol.19 , pp. 1813
    • Lai, G.1    Wang, S.2    Wang, Z.3
  • 54
    • 1842636561 scopus 로고    scopus 로고
    • Lipase catalysed resolution of nitro aldol adducts
    • DOI 10.1016/j.tetasy.2004.02.025, PII S0957416604001703
    • MJ Sorgedrager R Malpique FV Rantwijk RA Sheldon 2004 Tetrahedron Asymmetr 15 1295 1:CAS:528:DC%2BD2cXjtVCiur8%3D 10.1016/j.tetasy.2004.02.025 (Pubitemid 38479588)
    • (2004) Tetrahedron Asymmetry , vol.15 , Issue.8 , pp. 1295-1299
    • Sorgedrager, M.J.1    Malpique, R.2    Van Rantwijk, F.3    Sheldon, R.A.4
  • 55
    • 1842789682 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD2cXhvF2hsro%3D 10.1021/jo0358269
    • I Kudyba J Raczko J Jurczak 2004 J Org Chem 69 2844 1:CAS:528: DC%2BD2cXhvF2hsro%3D 10.1021/jo0358269
    • (2004) J Org Chem , vol.69 , pp. 2844
    • Kudyba, I.1    Raczko, J.2    Jurczak, J.3
  • 58
    • 78650173754 scopus 로고    scopus 로고
    • BlayG, Herna′ndez-Olmos V, Pedro J′R (2008) Chem Commun 4840
    • (2008) Chem Commun , pp. 4840
    • Blay G, H.1
  • 60
    • 34548532744 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD2sXos1Sltb8%3D 10.1021/ol7014362
    • T Arai M Watanabe A Yanagisawa 2007 Org Lett 9 3595 1:CAS:528: DC%2BD2sXos1Sltb8%3D 10.1021/ol7014362
    • (2007) Org Lett , vol.9 , pp. 3595
    • Arai, T.1    Watanabe, M.2    Yanagisawa, A.3
  • 62
    • 72049100940 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXhsFaku73O 10.1016/j.tetasy.2009.10.001
    • R Kowalczyk J Skarzewski 2009 Tetrahedron Asymmetr 20 2467 1:CAS:528:DC%2BD1MXhsFaku73O 10.1016/j.tetasy.2009.10.001
    • (2009) Tetrahedron Asymmetr , vol.20 , pp. 2467
    • Kowalczyk, R.1    Skarzewski, J.2
  • 65
    • 55549100907 scopus 로고    scopus 로고
    • Chiral binuclear copper(II) catalyzed nitroaldol reaction: Scope and mechanism
    • DOI 10.1016/j.tet.2008.10.009, PII S0040402008017742
    • S Jammi P Saha S Sanyashi T Punniyamurthy 2008 Tetrahedron 64 11724 1:CAS:528:DC%2BD1cXhtlyqurvI 10.1016/j.tet.2008.10.009 (Pubitemid 50311760)
    • (2008) Tetrahedron , vol.64 , Issue.51 , pp. 11724-11731
    • Jammi, S.1    Saha, P.2    Sanyashi, S.3    Sakthivel, S.4    Punniyamurthy, T.5
  • 66
    • 27544433063 scopus 로고    scopus 로고
    • Guanidine-thiourea bifunctional organocatalyst for the asymmetric Henry (nitroaldol) reaction
    • DOI 10.1002/adsc.200505148
    • Y Sohtome Y Hashimoto K Nagasawa 2005 Adv Synth Catal 347 1643 1:CAS:528:DC%2BD2MXht1ansLrK 10.1002/adsc.200505148 (Pubitemid 41542809)
    • (2005) Advanced Synthesis and Catalysis , vol.347 , Issue.11-13 , pp. 1643-1648
    • Sohtome, Y.1    Hashimoto, Y.2    Nagasawa, K.3
  • 68
    • 1542345592 scopus 로고    scopus 로고
    • Cetyltrimethylammonium hydroxide (CTAOH) as a general, ecofriendly catalyst for the formation of carbon-carbon bond through nitroalkanes
    • DOI 10.1016/j.tet.2004.01.067, PII S0040402004001450
    • R Ballini D Fiorini MV Gil A Palmieri 2004 Tetrahedron 60 2799 1:CAS:528:DC%2BD2cXhslWltr4%3D 10.1016/j.tet.2004.01.067 (Pubitemid 38299301)
    • (2004) Tetrahedron , vol.60 , Issue.12 , pp. 2799-2804
    • Ballini, R.1    Fiorini, D.2    Gil, M.V.3    Palmieri, A.4
  • 69
    • 33645242012 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD28XjvVCgtr0%3D 10.5012/bkcs.2006.27.3.345
    • YR Jorapur DY Chi 2006 Bull Korean Chem Soc 27 345 1:CAS:528: DC%2BD28XjvVCgtr0%3D 10.5012/bkcs.2006.27.3.345
    • (2006) Bull Korean Chem Soc , vol.27 , pp. 345
    • Jorapur, Y.R.1    Chi, D.Y.2
  • 71
    • 27344435269 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD2MXhtFGqtLrM 10.5012/bkcs.2005.26.9.1321
    • CE Song MY Yoon DS Choi 2005 Bull Korean Chem Soc 26 1321 1:CAS:528:DC%2BD2MXhtFGqtLrM 10.5012/bkcs.2005.26.9.1321
    • (2005) Bull Korean Chem Soc , vol.26 , pp. 1321
    • Song, C.E.1    Yoon, M.Y.2    Choi, D.S.3
  • 72
    • 28444494771 scopus 로고    scopus 로고
    • Immobilisation of chiral catalysts: Easy recycling of catalyst and improvement of catalytic efficiencies
    • DOI 10.1039/b408828j
    • CE Song 2005 Ann Rep Prog Chem 101 143 1:CAS:528:DC%2BD2MXhtFGrtL%2FI 10.1039/b408828j (Pubitemid 41735946)
    • (2005) Annual Reports on the Progress of Chemistry - Section C , vol.101 , pp. 143-173
    • Choong, E.S.1

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.