메뉴 건너뛰기




Volumn 22, Issue 1, 2010, Pages 173-181

Chiral amino amides for the ruthenium(II)-catalyzed asymmetric transfer hydrogenation reaction of ketones in water

Author keywords

Asymmetric transfer hydrogenation; Enantioselectivity; Ketones; Ruthenium; Water

Indexed keywords

[RUTHENIUM CHLORIDE(P CYMENE)]; AMIDE; KETONE DERIVATIVE; LIGAND; PROLINE; RUTHENIUM; UNCLASSIFIED DRUG; WATER;

EID: 75449105207     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20723     Document Type: Article
Times cited : (20)

References (36)
  • 2
    • 0141800091 scopus 로고    scopus 로고
    • Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of carbonyl compounds with 2-propanol and ephedrine-type ligands
    • Everaere K, Mortreux A, Carpentier JF. Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of carbonyl compounds with 2-propanol and ephedrine-type ligands. Adv Synth Catal 2003;345:67-77.
    • (2003) Adv Synth Catal , vol.345 , pp. 67-77
    • Everaere, K.1    Mortreux, A.2    Carpentier, J.F.3
  • 3
    • 0037908003 scopus 로고    scopus 로고
    • Homogeneous-supported catalysts for enantioselective hydrogenation and hydrogen transfer reduction
    • Saluzzo C, Lemaire M. Homogeneous-supported catalysts for enantioselective hydrogenation and hydrogen transfer reduction. Adv Synth Catal 2002;344:915-928.
    • (2002) Adv Synth Catal , vol.344 , pp. 915-928
    • Saluzzo, C.1    Lemaire, M.2
  • 4
    • 0036810665 scopus 로고    scopus 로고
    • Recoverable catalysts for asymmetric organic synthesis
    • Fan QH, Li YM, Chan ASC. Recoverable catalysts for asymmetric organic synthesis. Chem Rev 2002;102:3385-3466.
    • (2002) Chem Rev , vol.102 , pp. 3385-3466
    • Fan, Q.H.1    Li, Y.M.2    Chan, A.S.C.3
  • 5
    • 0033522739 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of C=O and C=N bonds
    • Palmer MJ, Wills M. Asymmetric transfer hydrogenation of C=O and C=N bonds. Tetrahedron Asymmetry 1999;10:2045-2061.
    • (1999) Tetrahedron Asymmetry , vol.10 , pp. 2045-2061
    • Palmer, M.J.1    Wills, M.2
  • 6
    • 0002123299 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes
    • 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
  • 7
    • 4243378570 scopus 로고
    • Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts
    • Zassinovich G, Mestroni G, Gladiali S. Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts. Chem Rev 1992;92:1051-1069.
    • (1992) Chem Rev , vol.92 , pp. 1051-1069
    • Zassinovich, G.1    Mestroni, G.2    Gladiali, S.3
  • 8
    • 33644660116 scopus 로고    scopus 로고
    • Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions
    • Gladiali S, Alberico E. Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions. Chem Soc Rev 2006;35:237-248.
    • (2006) Chem Soc Rev , vol.35 , pp. 237-248
    • Gladiali, S.1    Alberico, E.2
  • 9
    • 0001040853 scopus 로고    scopus 로고
    • Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R. Asymmetric transfer hydrogenation of aromatic ketones catalyzed by chiral ruthenium(II) complexes. J Am Chem Soc 1995;117:7562-7563.
    • Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R. Asymmetric transfer hydrogenation of aromatic ketones catalyzed by chiral ruthenium(II) complexes. J Am Chem Soc 1995;117:7562-7563.
  • 10
    • 0029879373 scopus 로고    scopus 로고
    • Ruthenium (II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture
    • Fujii A, Hashiguchi S, Uematsu N, Ikariya T, Noyori R. Ruthenium (II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture. J Am Chem Soc 1996;118:2521-2522.
    • (1996) J Am Chem Soc , vol.118 , pp. 2521-2522
    • Fujii, A.1    Hashiguchi, S.2    Uematsu, N.3    Ikariya, T.4    Noyori, R.5
  • 11
    • 0037033235 scopus 로고    scopus 로고
    • Use of surfactants in water-soluble ruthenium(II) complex-catalyzed asymmetric hydrogen-transfer reduction of aromatic ketones
    • Rhyoo HY, Park HJ, Suh WH, Chung YK. Use of surfactants in water-soluble ruthenium(II) complex-catalyzed asymmetric hydrogen-transfer reduction of aromatic ketones. Tetrahedron Lett 2002;43:269-272.
    • (2002) Tetrahedron Lett , vol.43 , pp. 269-272
    • Rhyoo, H.Y.1    Park, H.J.2    Suh, W.H.3    Chung, Y.K.4
  • 12
    • 0035929725 scopus 로고    scopus 로고
    • The first Ru(II)-catalysed asymmetric hydrogen transfer reduction of aromatic ketones in aqueous media
    • Rhyoo HY, Park HJ, Chung YK. The first Ru(II)-catalysed asymmetric hydrogen transfer reduction of aromatic ketones in aqueous media. Chem Commun 2001;2064-2065.
    • (2001) Chem Commun , pp. 2064-2065
    • Rhyoo, H.Y.1    Park, H.J.2    Chung, Y.K.3
  • 13
    • 39149106114 scopus 로고    scopus 로고
    • Aqueous asymmetric transfer hydrogenations using modular hydrophobic aminoalcohols
    • Alza E, Bastero A, Jansat S, Pericàs MA. Aqueous asymmetric transfer hydrogenations using modular hydrophobic aminoalcohols. Tetrahedron Asymmetry 2008;19:374-378.
    • (2008) Tetrahedron Asymmetry , vol.19 , pp. 374-378
    • Alza, E.1    Bastero, A.2    Jansat, S.3    Pericàs, M.A.4
  • 14
    • 25444519747 scopus 로고    scopus 로고
    • First example of asymmetric transfer hydrogenation in water induced by a chiral amino alcohol hydrochloride
    • Mao JC, Wan BS, Wu F, Lu SW. First example of asymmetric transfer hydrogenation in water induced by a chiral amino alcohol hydrochloride. Tetrahedron Lett 2005;46:7341-7344.
    • (2005) Tetrahedron Lett , vol.46 , pp. 7341-7344
    • Mao, J.C.1    Wan, B.S.2    Wu, F.3    Lu, S.W.4
  • 15
    • 38849086737 scopus 로고    scopus 로고
    • Inversion of stereochemistry in the asymmetric transfer hydrogenation of ketones performed in tap water and in open-vessel
    • Xu Z, Mao JC, Zhang YW, Guo J, Zhu JL. Inversion of stereochemistry in the asymmetric transfer hydrogenation of ketones performed in tap water and in open-vessel. Catal Commun 2008;9:618-623.
    • (2008) Catal Commun , vol.9 , pp. 618-623
    • Xu, Z.1    Mao, J.C.2    Zhang, Y.W.3    Guo, J.4    Zhu, J.L.5
  • 17
    • 34250201122 scopus 로고    scopus 로고
    • Aqeous-phase asymmetric transfer hydrogenation of ketones - A greener approach to chiral alcohols
    • Wu X, Xiao J. Aqeous-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
  • 18
    • 39149106114 scopus 로고    scopus 로고
    • Aqueous asymmetric transfer hydrogenations using modular hydrophobic aminoalcohols
    • Alza E, Bastero A, Jansat S, Pericàs MA. Aqueous asymmetric transfer hydrogenations using modular hydrophobic aminoalcohols. Tetrahedron Asymmetry 2008;19:374-378.
    • (2008) Tetrahedron Asymmetry , vol.19 , pp. 374-378
    • Alza, E.1    Bastero, A.2    Jansat, S.3    Pericàs, M.A.4
  • 19
  • 20
    • 55049120804 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of aromatic ketones in water using a polymer-supported chiral catalyst containing a hydrophilic pendant group
    • Arakawa Y, Chiba A, Haraguchi N, Itsuno S. Asymmetric transfer hydrogenation of aromatic ketones in water using a polymer-supported chiral catalyst containing a hydrophilic pendant group. Adv Synth Catal 2008;350:2295-2304.
    • (2008) Adv Synth Catal , vol.350 , pp. 2295-2304
    • Arakawa, Y.1    Chiba, A.2    Haraguchi, N.3    Itsuno, S.4
  • 21
    • 6344276857 scopus 로고    scopus 로고
    • Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in water
    • Liu PN, Deng JG, Tu YQ, Wang SH. Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in water. Chem Commun 2004;2070-2071.
    • (2004) Chem Commun , pp. 2070-2071
    • Liu, P.N.1    Deng, J.G.2    Tu, Y.Q.3    Wang, S.H.4
  • 22
    • 43049116112 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of ketones with a polyethylene glycol bound Ru catalyst in water
    • Liu J, Zhou Y, Wu Y, Li X, Chan ASC. Asymmetric transfer hydrogenation of ketones with a polyethylene glycol bound Ru catalyst in water. Tetrahedron Asymmetry 2008;19:832-837.
    • (2008) Tetrahedron Asymmetry , vol.19 , pp. 832-837
    • Liu, J.1    Zhou, Y.2    Wu, Y.3    Li, X.4    Chan, A.S.C.5
  • 23
    • 47049114954 scopus 로고    scopus 로고
    • Cortez NA, Aguirre G, Parra-Hake M, Somanathan R. Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)- diaminocyclohexane. Tetrahedron Asymmetry 2008;19:1304-1309.
    • Cortez NA, Aguirre G, Parra-Hake M, Somanathan R. Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)- diaminocyclohexane. Tetrahedron Asymmetry 2008;19:1304-1309.
  • 24
    • 34047098387 scopus 로고    scopus 로고
    • Water-soluble arene ruthenium catalysts containing sulfonated diamine ligands for asymmetric transfer hydrogenation of α-aryl ketones and imines in aqueous solution
    • Canivet J, Suss-Fink G. Water-soluble arene ruthenium catalysts containing sulfonated diamine ligands for asymmetric transfer hydrogenation of α-aryl ketones and imines in aqueous solution. Green Chem 2007;9:391-397.
    • (2007) Green Chem , vol.9 , pp. 391-397
    • Canivet, J.1    Suss-Fink, G.2
  • 25
    • 33845977402 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of ketones and imines with novel water-soluble chiral diamine as ligand in neat water
    • Li L, Wu JS, Fang F, Liao J, Zhang H, Lian CX, Zhu J, Deng JG. Asymmetric transfer hydrogenation of ketones and imines with novel water-soluble chiral diamine as ligand in neat water. Green Chem 2007;9:23-25.
    • (2007) Green Chem , vol.9 , pp. 23-25
    • Li, L.1    Wu, J.S.2    Fang, F.3    Liao, J.4    Zhang, H.5    Lian, C.X.6    Zhu, J.7    Deng, J.G.8
  • 26
    • 33847318741 scopus 로고    scopus 로고
    • Asymmetric reactions on chiral catalysts entrapped within a mesoporous cage
    • Yang HQ, Li J, Yang J, Liu ZM, Yang QH, Li C. Asymmetric reactions on chiral catalysts entrapped within a mesoporous cage. Chem Commun 2007;1086-1088.
    • (2007) Chem Commun , pp. 1086-1088
    • Yang, H.Q.1    Li, J.2    Yang, J.3    Liu, Z.M.4    Yang, Q.H.5    Li, C.6
  • 27
    • 33646944868 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water
    • Wu JS, Wang F, Ma YP, Cui XC, Cun LF, Zhu J, Deng JG, Yu BL. Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water. Chem Commun 2006;1766-1768.
    • (2006) Chem Commun , pp. 1766-1768
    • Wu, J.S.1    Wang, F.2    Ma, Y.P.3    Cui, X.C.4    Cun, L.F.5    Zhu, J.6    Deng, J.G.7    Yu, B.L.8
  • 28
    • 33646775701 scopus 로고    scopus 로고
    • Highly efficient chiral PNNP ligand for asymmetric transfer hydrogenation of aromatic ketones in water
    • Xing Y, Chen JS, Dong ZR, Li YY, Gao JX. Highly efficient chiral PNNP ligand for asymmetric transfer hydrogenation of aromatic ketones in water. Tetrahedron Lett 2006;47:4501-4503.
    • (2006) Tetrahedron Lett , vol.47 , pp. 4501-4503
    • Xing, Y.1    Chen, J.S.2    Dong, Z.R.3    Li, Y.Y.4    Gao, J.X.5
  • 29
    • 33746448277 scopus 로고    scopus 로고
    • An outstanding catalyst for asymmetric transfer hydrogenation in aqueous solution and formic acid/triethylamine
    • Matharu DS, Morris DJ, Klarkson GJ, Wills M. An outstanding catalyst for asymmetric transfer hydrogenation in aqueous solution and formic acid/triethylamine. Chem Commun 2006;3232-3234.
    • (2006) Chem Commun , pp. 3232-3234
    • Matharu, D.S.1    Morris, D.J.2    Klarkson, G.J.3    Wills, M.4
  • 30
    • 33747875751 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation catalysed by hydrophobic dendritic DACH-rhodium complex in water
    • Jiang L, Wu TF, Chen YC, Zhu J, Deng JG. Asymmetric transfer hydrogenation catalysed by hydrophobic dendritic DACH-rhodium complex in water. Org Biomol Chem 2006;4:3319-3324.
    • (2006) Org Biomol Chem , vol.4 , pp. 3319-3324
    • Jiang, L.1    Wu, T.F.2    Chen, Y.C.3    Zhu, J.4    Deng, J.G.5
  • 31
    • 0141854157 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand
    • 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
  • 33
    • 0345239364 scopus 로고
    • II) with 2-aminocarbonylpyrrolidine ligands. Selective catalysts for hydrogenation of prochiral olefins
    • II) with 2-aminocarbonylpyrrolidine ligands. Selective catalysts for hydrogenation of prochiral olefins. J Organometallic Chem 1992;431:233-246.
    • (1992) J Organometallic Chem , vol.431 , pp. 233-246
    • Corma, A.1    Iglesias, M.2    del Pino, C.3    Sánchez, F.4
  • 34
    • 33747755747 scopus 로고    scopus 로고
    • Small organic molecule catalyzed enantioselective direct aldol reaction in water
    • Chimni SS, Mahajan D. Small organic molecule catalyzed enantioselective direct aldol reaction in water. Tetrahedron Asymmetry 2006;17:2108-2119.
    • (2006) Tetrahedron Asymmetry , vol.17 , pp. 2108-2119
    • Chimni, S.S.1    Mahajan, D.2
  • 35
    • 38349193137 scopus 로고    scopus 로고
    • Evaluation of ligands for ketone reduction by asymmetric hydride transfer in water by mutisubstrate screening
    • Zeror S, Collin J, Fiaud JC, Zouioueche LA. Evaluation of ligands for ketone reduction by asymmetric hydride transfer in water by mutisubstrate screening. Adv Synth Catal 2008;350:197-204.
    • (2008) Adv Synth Catal , vol.350 , pp. 197-204
    • Zeror, S.1    Collin, J.2    Fiaud, J.C.3    Zouioueche, L.A.4
  • 36
    • 33744491804 scopus 로고    scopus 로고
    • An efficient Ir(III) catalyst for the asymmetric hydrogenation of ketones in neat water
    • Li XH, Blacker J, Houson I, Wu XF, Xiao JL. An efficient Ir(III) catalyst for the asymmetric hydrogenation of ketones in neat water. Synlett 2006;8:1155-1160.
    • (2006) Synlett , vol.8 , pp. 1155-1160
    • Li, X.H.1    Blacker, J.2    Houson, I.3    Wu, X.F.4    Xiao, J.L.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.