메뉴 건너뛰기




Volumn 39, Issue 15, 2009, Pages 2737-2746

Synthesis of chiral aromatic alcohols: Use of new C2-symmetric RhIIICp*, RuII(cymene), or RuII(benzene) complexes containing chiral diaminocyclohexane ligand as asymmetric transfer hydrogenation catalyst

Author keywords

Bis(sulfonamide) ligands; Chiral secondary alcohols; RhIIICp*; RuII(arene)

Indexed keywords

2 PROPANOL; ALCOHOL DERIVATIVE; BENZENE DERIVATIVE; BIS(SULFONAMIDE); CYCLOHEXANE 1,2 DIAMINE; CYCLOHEXYLAMINE DERIVATIVE; DIAMINE DERIVATIVE; DIAMINOCYCLOHEXANE; FORMATE SODIUM; FORMIC ACID DERIVATIVE; KETONE; LIGAND; PARA CYMENE; RHENIUM COMPLEX; RUTHENIUM COMPLEX; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 67650327120     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802663451     Document Type: Article
Times cited : (11)

References (40)
  • 2
    • 0004564599 scopus 로고
    • Academic Press: New York, vols
    • (b) Morrison, J. D. Asymmetric Synthesis; Academic Press: New York, 1983-1985; vols. 1- 5;
    • (1983) Asymmetric Synthesis , vol.1 , pp. 5
    • Morrison, J.D.1
  • 4
    • 0002634798 scopus 로고    scopus 로고
    • Asymmetric hydrogenation
    • 2nd ed, I. Ojima Ed, John Wiley and Sons: New York
    • (a) Ohkuma, T.; Kitamura, M.; Noyori, R. Asymmetric hydrogenation; In Catalytic Asymmetric Synthesis, 2nd ed., I. Ojima (Ed.); John Wiley and Sons: New York, 2000, pp. 1-110;
    • (2000) Catalytic Asymmetric Synthesis , pp. 1-110
    • Ohkuma, T.1    Kitamura, M.2    Noyori, R.3
  • 5
    • 4243378570 scopus 로고
    • Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes
    • (b) Zassinovich, G.; Mestroni, G.; Gladiali, S. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Chem. Rev. 1992, 92, 1051-1069;
    • (1992) Chem. Rev , vol.92 , pp. 1051-1069
    • Zassinovich, G.1    Mestroni, G.2    Gladiali, S.3
  • 6
    • 0032541271 scopus 로고    scopus 로고
    • Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method
    • (c) Corey, E. J.; Helal, C. J. Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method. Angew. Chem. Int. Ed. 1998, 37, 1986-2012;
    • (1998) Angew. Chem. Int. Ed , vol.37 , pp. 1986-2012
    • Corey, E.J.1    Helal, C.J.2
  • 7
    • 0002123299 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes
    • (d) Noyori, R.; Hashiguchi, S. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Acc.Chem. Res. 1997, 30, 97-102;
    • (1997) Acc.Chem. Res , vol.30 , pp. 97-102
    • Noyori, R.1    Hashiguchi, S.2
  • 8
    • 33645681534 scopus 로고    scopus 로고
    • Bifunctional transition metal-based molecular catalysts for asymmetric syntheses
    • (e) Ikariya, T.; Murata, K.; Noyori, R. Bifunctional transition metal-based molecular catalysts for asymmetric syntheses. Org. Biomol. Chem. 2006, 4, 393-406.
    • (2006) Org. Biomol. Chem , vol.4 , pp. 393-406
    • Ikariya, T.1    Murata, K.2    Noyori, R.3
  • 10
    • 0032568230 scopus 로고    scopus 로고
    • Conformational toolbox of oxazaborolidine catalysts in the enantioselective reduction of α-bromo-ketone for the synthesis of (R,R)-formoterol
    • (b) Hett, R.; Senanayake, C. H.; Wald, S. A. Conformational toolbox of oxazaborolidine catalysts in the enantioselective reduction of α-bromo-ketone for the synthesis of (R,R)-formoterol. Tetrahedron Lett. 1998, 39, 1705-1708;
    • (1998) Tetrahedron Lett , vol.39 , pp. 1705-1708
    • Hett, R.1    Senanayake, C.H.2    Wald, S.A.3
  • 11
    • 19344372011 scopus 로고    scopus 로고
    • Polymer-supported chiral sulfonamide catalyzed one-pot reduction of β-keto nitriles: A practical synthesis of (R)-fluoxetine and (R)-duloxetine
    • (c) Wang, G.; Liu, X.; Zhao, G. Polymer-supported chiral sulfonamide catalyzed one-pot reduction of β-keto nitriles: A practical synthesis of (R)-fluoxetine and (R)-duloxetine. Tetrahedron: Asymmetry 2005, 16, 1873-1879;
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1873-1879
    • Wang, G.1    Liu, X.2    Zhao, G.3
  • 12
    • 13844275569 scopus 로고    scopus 로고
    • An efficient catalytic asymmetric route to 1-aryl-2-imidazol-1-yl-ethanols
    • (d) Lennon, I. C.; Ramsden, J. A. An efficient catalytic asymmetric route to 1-aryl-2-imidazol-1-yl-ethanols. Org. Process. Res. Dev. 2005, 9, 110-112;
    • (2005) Org. Process. Res. Dev , vol.9 , pp. 110-112
    • Lennon, I.C.1    Ramsden, J.A.2
  • 13
    • 0037474676 scopus 로고    scopus 로고
    • Reilly, M.; Anthony, D. R.; Gallagher, C. Concise, enantiospecific synthesis of (3S,4R)-3-amino-4- ethylpiperidine as partner to a non-fluoroquinolone nucleus. Tetrahedron Lett. 2003, 44, 2927-2930;
    • (e) Reilly, M.; Anthony, D. R.; Gallagher, C. Concise, enantiospecific synthesis of (3S,4R)-3-amino-4- ethylpiperidine as partner to a non-fluoroquinolone nucleus. Tetrahedron Lett. 2003, 44, 2927-2930;
  • 14
    • 0034716021 scopus 로고    scopus 로고
    • Stereoselective synthesis of optically active pyridyl alcohols via asymmetric transfer hydrogenation of pyridyl ketones
    • (f) Okano, K.; Murata, K.; Ikariya, T. Stereoselective synthesis of optically active pyridyl alcohols via asymmetric transfer hydrogenation of pyridyl ketones. Tetrahedron Lett. 2000, 41, 9277-9280.
    • (2000) Tetrahedron Lett , vol.41 , pp. 9277-9280
    • Okano, K.1    Murata, K.2    Ikariya, T.3
  • 15
    • 4143105564 scopus 로고    scopus 로고
    • Synthesis of substituted mandelic acid derivatives via enantioselective hydrogenation: Homogeneous versus heterogeneous catalysis
    • Cederbaum, F.; Lamberth, C.; Malan, C.; Naud, F.; Spindler, F.; Studer, M.; Blazer, H.-U. Synthesis of substituted mandelic acid derivatives via enantioselective hydrogenation: Homogeneous versus heterogeneous catalysis. Adv. Synth. Catal. 2004, 346, 842-848.
    • (2004) Adv. Synth. Catal , vol.346 , pp. 842-848
    • Cederbaum, F.1    Lamberth, C.2    Malan, C.3    Naud, F.4    Spindler, F.5    Studer, M.6    Blazer, H.-U.7
  • 16
    • 0343619436 scopus 로고    scopus 로고
    • Synthesis of (R)- and (S)-4- hydroxyisophorone by ruthenium-catalyzed asymmetric transfer hydrogenation of ketoisophorone
    • Hennig, M.; Pü ntener, K.; Scalone, M. Synthesis of (R)- and (S)-4- hydroxyisophorone by ruthenium-catalyzed asymmetric transfer hydrogenation of ketoisophorone. Tetrahedron: Asymmetry 2000, 11, 1849-1858.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1849-1858
    • Hennig, M.1    Pü ntener, K.2    Scalone, M.3
  • 17
    • 38049002421 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts
    • (a) Ikariya, T.; Blacker, A. J. Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. Acc. Chem. Res. 2007, 40, 1300-1308;
    • (2007) Acc. Chem. Res , vol.40 , pp. 1300-1308
    • Ikariya, T.1    Blacker, A.J.2
  • 18
    • 38049004864 scopus 로고    scopus 로고
    • Developments in asymmetric hydrogenation from an industrial perspective
    • (b) Shimizu, H.; Nagasaki, I.; Matsumura, K.; Sayo, N.; Saito, T. Developments in asymmetric hydrogenation from an industrial perspective. Acc. Chem. Res. 2007, 40, 1385-1393;
    • (2007) Acc. Chem. Res , vol.40 , pp. 1385-1393
    • Shimizu, H.1    Nagasaki, I.2    Matsumura, K.3    Sayo, N.4    Saito, T.5
  • 19
    • 38049059816 scopus 로고    scopus 로고
    • Industrial-scale synthesis and applications of asymmetric hydrogenation catalysts
    • (c) Johnson, N. B.; Lennon, I. S.; Moran, P. H.; Ramsden, J. A. Industrial-scale synthesis and applications of asymmetric hydrogenation catalysts. Acc. Chem. Res, 2007, 40, 1291-1299;
    • (2007) Acc. Chem. Res , vol.40 , pp. 1291-1299
    • Johnson, N.B.1    Lennon, I.S.2    Moran, P.H.3    Ramsden, J.A.4
  • 21
    • 0002123299 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes
    • (a) Noyori, R.; Hashiguchi, S. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Acc. Chem. Res. 1997, 30, 97-102;
    • (1997) Acc. Chem. Res , vol.30 , pp. 97-102
    • Noyori, R.1    Hashiguchi, S.2
  • 22
    • 5444236447 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of α-aminoalkyl a0-chloromethyl ketones with chiral Rh complexes
    • (b) Hamada, T.; Torii, T.; Onishi, T.; Izawa, K.; Ikariya, T. Asymmetric transfer hydrogenation of α-aminoalkyl a0-chloromethyl ketones with chiral Rh complexes. J. Org. Chem. 2004, 69, 7391-7394;
    • (2004) J. Org. Chem , vol.69 , pp. 7391-7394
    • Hamada, T.1    Torii, T.2    Onishi, T.3    Izawa, K.4    Ikariya, T.5
  • 23
    • 0037040674 scopus 로고    scopus 로고
    • Practical synthesis of optically active amino alcohols via asymmetric transfer hydrogenation of functionalized aromatic ketones
    • (c) Watanabe, M.; Murata, K.; Ikariya, T. Practical synthesis of optically active amino alcohols via asymmetric transfer hydrogenation of functionalized aromatic ketones. J. Org. Chem. 2002, 67, 1712-1715;
    • (2002) J. Org. Chem , vol.67 , pp. 1712-1715
    • Watanabe, M.1    Murata, K.2    Ikariya, T.3
  • 24
    • 0034736377 scopus 로고    scopus 로고
    • Stereoselective synthesis of optically active α-hydroxy ketones and anti-1,2- diols via asymmetric transfer hydrogenation of unsymmetrically substituted 1,2-diketones
    • (d) Koike, T.; Murata, K.; Ikariya, T. Stereoselective synthesis of optically active α-hydroxy ketones and anti-1,2- diols via asymmetric transfer hydrogenation of unsymmetrically substituted 1,2-diketones. Org. Lett. 2000, 2, 3833-3836;
    • (2000) Org. Lett , vol.2 , pp. 3833-3836
    • Koike, T.1    Murata, K.2    Ikariya, T.3
  • 25
    • 0042497321 scopus 로고    scopus 로고
    • Asymmetric catalysis: Science and opportunities (Nobel Lecture 2001)
    • (e) Noyori, R. Asymmetric catalysis: Science and opportunities (Nobel Lecture 2001). Adv. Synth. Catal.2003, 345, 15-32;
    • (2003) Adv. Synth. Catal , vol.345 , pp. 15-32
    • Noyori, R.1
  • 26
    • 37649026044 scopus 로고    scopus 로고
    • Asymmetric catalysis by architectural and functional molecular engineering: Practical chemo- and stereoselective hydrogenation of ketones
    • (f) Noyori, R.; Ohkuma, T. Asymmetric catalysis by architectural and functional molecular engineering: Practical chemo- and stereoselective hydrogenation of ketones. Angew. Chem. Int. Ed. 2001, 40, 40-73;
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 40-73
    • Noyori, R.1    Ohkuma, T.2
  • 27
    • 33644661038 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation: Chiral ligands and applications
    • (g) Gladiali, S.; Alberico, E. Asymmetric transfer hydrogenation: Chiral ligands and applications. Chem. Soc. Rev. 2006, 35, 226-236.
    • (2006) Chem. Soc. Rev , vol.35 , pp. 226-236
    • Gladiali, S.1    Alberico, E.2
  • 29
    • 34250201122 scopus 로고    scopus 로고
    • Aqueous-phase asymmetric transfer hydrogenation of ketones-A greener approach to chiral alcohols
    • (a) Wu, X.; Xiao, J. Aqueous-phase asymmetric transfer hydrogenation of ketones-A greener approach to chiral alcohols. Chem. Commun. 2007, 2449-2466;
    • (2007) Chem. Commun , pp. 2449-2466
    • Wu, X.1    Xiao, J.2
  • 30
    • 33750294019 scopus 로고    scopus 로고
    • 2-symmetric bis(sulfonamide)- cyclohexane-1,2-diamine-RhCp* complex and its application in the asymmetric transfer hydrogenation (ATH) of ketones in water
    • 2-symmetric bis(sulfonamide)- cyclohexane-1,2-diamine-RhCp* complex and its application in the asymmetric transfer hydrogenation (ATH) of ketones in water. Tetrahedron Lett. 2006, 47, 8515-8518.
    • (2006) Tetrahedron Lett , vol.47 , pp. 8515-8518
    • Cortez, N.A.1    Rodríguez-Apodaca, R.2    Aguirre, G.3    Parra- Hake, M.4    Cole, T.5    Somanathan, R.6
  • 31
    • 67650320811 scopus 로고    scopus 로고
    • Compared with a chloro alcohol sample from Aldrich Sigma, rotation (-) for configuration (R), based on rotation (+) the configuration (S) is assigned;
    • (a) Compared with a chloro alcohol sample from Aldrich Sigma, rotation (-) for configuration (R), based on rotation (+) the configuration (S) is assigned;
  • 32
    • 39749114888 scopus 로고    scopus 로고
    • Asymmetric reduction of chloroacetophenones to produce chiral alcohols with microorganisms
    • (b) Ou, Z.; Wu, J.; Yang, L.; Cen, P. Asymmetric reduction of chloroacetophenones to produce chiral alcohols with microorganisms. Korean J. Material Sci. Chem. Eng. 2008, 25, 124-128;
    • (2008) Korean J. Material Sci. Chem. Eng , vol.25 , pp. 124-128
    • Ou, Z.1    Wu, J.2    Yang, L.3    Cen, P.4
  • 33
    • 25444451617 scopus 로고    scopus 로고
    • A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air
    • (c) Wu, X.; Vinci, D.; Ikariya, T.; Xiao, J. A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air. Chem. Commun. 2005, 4447-4449;
    • (2005) Chem. Commun , pp. 4447-4449
    • Wu, X.1    Vinci, D.2    Ikariya, T.3    Xiao, J.4
  • 34
    • 0141854157 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand
    • (d) Ma, Y.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand. Org. Lett. 2003, 5, 2103-2106.
    • (2003) Org. Lett , vol.5 , pp. 2103-2106
    • Ma, Y.1    Liu, H.2    Chen, L.3    Cui, X.4    Zhu, J.5    Deng, J.6
  • 36
    • 53849095171 scopus 로고    scopus 로고
    • A multilateral mechanistic study into asymmetric transfer hydro genation in water
    • Wu, X.; Liu, J.; Di Tommaso, D.; Iggo, J. A.; Catlow, C. R. A.; Bacsa, J.; Xiao, J. A multilateral mechanistic study into asymmetric transfer hydro genation in water. Chem. A. Eur. J. 2008, 14, 7699-7715.
    • (2008) Chem. A. Eur. J , vol.14 , pp. 7699-7715
    • Wu, X.1    Liu, J.2    Di Tommaso, D.3    Iggo, J.A.4    Catlow, C.R.A.5    Bacsa, J.6    Xiao, J.7
  • 40
    • 0035898133 scopus 로고    scopus 로고
    • Ng, K.; Somanathan, R.; Walsh, P. J. Synthesis of homochiral pentadentate sulfonamide-based ligands. Tetrahedron: Asymmetry 2001, 12, 1719-1722.
    • Ng, K.; Somanathan, R.; Walsh, P. J. Synthesis of homochiral pentadentate sulfonamide-based ligands. Tetrahedron: Asymmetry 2001, 12, 1719-1722.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.