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Volumn 62, Issue 6, 2007, Pages 731-738

Nonlinear effects in enantioselective organometallic catalysis

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; MATHEMATICAL MODELS; NONLINEAR EQUATIONS;

EID: 38549089968     PISSN: 12944475     EISSN: None     Source Type: Journal    
DOI: 10.2516/ogst:2007051     Document Type: Article
Times cited : (8)

References (50)
  • 1
    • 0002788460 scopus 로고
    • Asymmetric synthesis caused by catalyts
    • Bredig, G. and Fiske, P.S. (1913) Asymmetric synthesis caused by catalyts. Biochem. Z., 46, 7-23.
    • (1913) Biochem. Z , vol.46 , pp. 7-23
    • Bredig, G.1    Fiske, P.S.2
  • 2
    • 0002157766 scopus 로고    scopus 로고
    • Historical perspective
    • For history of asymmetric catalysis see:, Jacobsen, E.N, Pfaltz, A. and Yamamoto, H, eds, Springer-Verlag, Berlin
    • For history of asymmetric catalysis see: Kagan, H.B. (1999) Historical perspective, in Comprehensive Asymmetric Catalysis, Jacobsen, E.N., Pfaltz, A. and Yamamoto, H. (eds.), Springer-Verlag, Berlin, Vol. 1, pp. 9-30.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 9-30
    • Kagan, H.B.1
  • 3
    • 0042625501 scopus 로고
    • Asymmetric synthesis of optically active di-isotactic polymers from cyclic monomers
    • Natta, G., Farina, M., Peraldo, M. and Bressan, G. (1961) Asymmetric synthesis of optically active di-isotactic polymers from cyclic monomers. Makromol. Chem., 43, 68-75.
    • (1961) Makromol. Chem , vol.43 , pp. 68-75
    • Natta, G.1    Farina, M.2    Peraldo, M.3    Bressan, G.4
  • 4
    • 49949143547 scopus 로고
    • Asymmetric induction in carbenoid reactions by means of a dissymmetric copper chelate
    • Nozaki, H., Moriuti, S., Takaya, H. and Noyori, R. (1966) Asymmetric induction in carbenoid reactions by means of a dissymmetric copper chelate. Tetrahedron Lett., 22, 5239-5244.
    • (1966) Tetrahedron Lett , vol.22 , pp. 5239-5244
    • Nozaki, H.1    Moriuti, S.2    Takaya, H.3    Noyori, R.4
  • 5
    • 33444462389 scopus 로고
    • Asymmetric hydrogenation employing a soluble, optically active, rhodium complex
    • Knowles, W.S. and Sabacky, M.J. (1968) Asymmetric hydrogenation employing a soluble, optically active, rhodium complex. Chem. Commun., 1445-1446.
    • (1968) Chem. Commun , pp. 1445-1446
    • Knowles, W.S.1    Sabacky, M.J.2
  • 6
    • 84981789229 scopus 로고
    • Asymmetric catalytic hydrogenation with an optically active phosphinerhodium complex in homogeneous solution
    • Horner, L, Siegel, H. and Büthe, H. (1968) Asymmetric catalytic hydrogenation with an optically active phosphinerhodium complex in homogeneous solution. Angew. Chem. Int. Edit. Engl., 7, 942.
    • (1968) Angew. Chem. Int. Edit. Engl , vol.7 , pp. 942
    • Horner, L.1    Siegel, H.2    Büthe, H.3
  • 7
    • 37049139019 scopus 로고
    • The asymmetric synthesis of hydratropic acid and amino acids by homogeneous catalytic hydrogenation
    • Dang, T.P. and Kagan, H.B. (1971) The asymmetric synthesis of hydratropic acid and amino acids by homogeneous catalytic hydrogenation. Chem. Commun., 481.
    • (1971) Chem. Commun , pp. 481
    • Dang, T.P.1    Kagan, H.B.2
  • 8
    • 33947089148 scopus 로고
    • Asymmetric catalytic reduction with transition metal complexes. -I. A catalytic system of rhodium(I) with (-)-2,3-O-isopropylidene-2,3-dihydroxy 1,4-(diphenylphosphino)butane, a new chiral diphosphine
    • Kagan, H.B. and Dang, T.P. (1972) Asymmetric catalytic reduction with transition metal complexes. -I. A catalytic system of rhodium(I) with (-)-2,3-O-isopropylidene-2,3-dihydroxy 1,4-(diphenylphosphino)butane, a new chiral diphosphine. J. Am. Chem. Soc., 94, 6429-6433.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 6429-6433
    • Kagan, H.B.1    Dang, T.P.2
  • 9
    • 84912849518 scopus 로고
    • Asymmetric catalysis by chiral rhodium complexes in hydrogenation and hydrosilylation reactions
    • Kagan, H.B. (1975) Asymmetric catalysis by chiral rhodium complexes in hydrogenation and hydrosilylation reactions. Pure Appl. Chem., 43, 401-421.
    • (1975) Pure Appl. Chem , vol.43 , pp. 401-421
    • Kagan, H.B.1
  • 10
    • 38549118093 scopus 로고    scopus 로고
    • Dang, T.P. and Kagan, H.B. (1970) Bidentate coordinates, their manufacture and application, Patent IFP, France, Dec. 10, 1970, US, Dec. 7, 1971, Ser. No. 205,744.
    • Dang, T.P. and Kagan, H.B. (1970) Bidentate coordinates, their manufacture and application, Patent IFP, France, Dec. 10, 1970, US, Dec. 7, 1971, Ser. No. 205,744.
  • 11
    • 33847800667 scopus 로고
    • Asymmetric hydrogenation with a complex of rhodium and a chiral biphosphine
    • Knowles, W.S., Sabacky, M., Vineyard, B.D. and Weinkauff, D.J. (1975) Asymmetric hydrogenation with a complex of rhodium and a chiral biphosphine. J. Am. Chem. Soc., 97, 2967-2968.
    • (1975) J. Am. Chem. Soc , vol.97 , pp. 2967-2968
    • Knowles, W.S.1    Sabacky, M.2    Vineyard, B.D.3    Weinkauff, D.J.4
  • 12
    • 0017774179 scopus 로고
    • Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation
    • Fryzuk, M.D. and Bosnich, B. (1977) Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation. J. Am. Chem. Soc., 99, 6262-6267.
    • (1977) J. Am. Chem. Soc , vol.99 , pp. 6262-6267
    • Fryzuk, M.D.1    Bosnich, B.2
  • 13
    • 49349137423 scopus 로고
    • Asymmetric hydrogenation by an atropoisomeric diphosphinite rhodium complex
    • Grubbs, R.H. and DeVries, R.A. (1977) Asymmetric hydrogenation by an atropoisomeric diphosphinite rhodium complex. Tetrahedron Lett., 18, 1879-1880.
    • (1977) Tetrahedron Lett , vol.18 , pp. 1879-1880
    • Grubbs, R.H.1    DeVries, R.A.2
  • 14
    • 1542694981 scopus 로고
    • Synthesis of 2,2'-bis(diphenylphosphino)-1, 1'-bis-naphthyl (BINAP), an atropoisomeric chiral bis(triaryl)phosphine and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of β-aminoacrylic acids
    • Miyashita, A., Yasuda, A., Takaya, H., Toriumi, K., Ito, T., Souji, T. and Noyori, R. (1980) Synthesis of 2,2'-bis(diphenylphosphino)-1, 1'-bis-naphthyl (BINAP), an atropoisomeric chiral bis(triaryl)phosphine and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of β-aminoacrylic acids. J. Am. Chem. Soc., 102, 7932-7934.
    • (1980) J. Am. Chem. Soc , vol.102 , pp. 7932-7934
    • Miyashita, A.1    Yasuda, A.2    Takaya, H.3    Toriumi, K.4    Ito, T.5    Souji, T.6    Noyori, R.7
  • 15
    • 0034079675 scopus 로고    scopus 로고
    • Chiral morrophosphines as ligands for asymmetric catalysis
    • Lagasse, F. and Kagan, H.B. (2000) Chiral morrophosphines as ligands for asymmetric catalysis. Chem. Pharm. Bull., 48, 315-324.
    • (2000) Chem. Pharm. Bull , vol.48 , pp. 315-324
    • Lagasse, F.1    Kagan, H.B.2
  • 16
    • 0034602040 scopus 로고    scopus 로고
    • Highly enantioselective Rh-catalyzed hydrogenation reactions based on chiral monophosphite ligands
    • Reetz, M. and Mehler, G. (2000) Highly enantioselective Rh-catalyzed hydrogenation reactions based on chiral monophosphite ligands. Angew. Chem. Int. Edit., 39, 3889-3890.
    • (2000) Angew. Chem. Int. Edit , vol.39 , pp. 3889-3890
    • Reetz, M.1    Mehler, G.2
  • 18
    • 0000025972 scopus 로고    scopus 로고
    • Asymmetric amplification
    • Denmark, S. Ed
    • Kagan, H.B. and Fenwick, D.R. (1999) Asymmetric amplification. Topics Stereochem., Denmark, S. Ed., 22, 257-296.
    • (1999) Topics Stereochem , vol.22 , pp. 257-296
    • Kagan, H.B.1    Fenwick, D.R.2
  • 20
    • 33845374428 scopus 로고
    • Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidation and aldolization reactions
    • Puchot, C., Samuel, O., Dunach, E., Zhao, S., Agami, C. and Kagan, H.B. (1986) Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidation and aldolization reactions. J. Am. Chem. Soc., 108, 2353-2357.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 2353-2357
    • Puchot, C.1    Samuel, O.2    Dunach, E.3    Zhao, S.4    Agami, C.5    Kagan, H.B.6
  • 21
    • 33845279196 scopus 로고
    • Asymmetric amplifying phenomena in enantioselective addition of diethylzinc to benzadehyde
    • Oguni, N., Matsuda, Y. and Kaneko, T. (1988) Asymmetric amplifying phenomena in enantioselective addition of diethylzinc to benzadehyde. J. Am. Chem. Soc., 110, 7877-7878.
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 7877-7878
    • Oguni, N.1    Matsuda, Y.2    Kaneko, T.3
  • 23
    • 0037425534 scopus 로고    scopus 로고
    • Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition state of praline catalyzed intra- and intermolecular aldol reactions
    • Hoang, L., Bahmanayar, S., Houk, K.N. and List, B. (2003) Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition state of praline catalyzed intra- and intermolecular aldol reactions. J. Am. Chem. Soc., 125, 16-17.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 16-17
    • Hoang, L.1    Bahmanayar, S.2    Houk, K.N.3    List, B.4
  • 24
    • 4544276855 scopus 로고    scopus 로고
    • Amplification of enantiomeric excess in a proline-mediated reaction
    • Mathew, S.P., Iwamura, H. and Blackmond, D.G. (2006) Amplification of enantiomeric excess in a proline-mediated reaction. Angew. Chem. Int. Edit., 43, 3317-3321.
    • (2006) Angew. Chem. Int. Edit , vol.43 , pp. 3317-3321
    • Mathew, S.P.1    Iwamura, H.2    Blackmond, D.G.3
  • 25
    • 0032538773 scopus 로고    scopus 로고
    • Nonlinear effects in asymmetric synthesis and stereoselective reactions: Ten years of investigation
    • Girard, C. and Kagan, H.B. (1998) Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew. Chem. Int. Edit. Engl., 37, 2922-2959.
    • (1998) Angew. Chem. Int. Edit. Engl , vol.37 , pp. 2922-2959
    • Girard, C.1    Kagan, H.B.2
  • 26
    • 0034977429 scopus 로고    scopus 로고
    • Nonlinear effects in asymmetric catalysis: A personal account
    • Kagan, H.B. (2001) Nonlinear effects in asymmetric catalysis: a personal account. Synlett, 888-900.
    • (2001) Synlett , pp. 888-900
    • Kagan, H.B.1
  • 27
    • 0001704921 scopus 로고    scopus 로고
    • Practical consequences of nonlinear effects in asymmetric synthesis
    • Kagan, H.B. (2001) Practical consequences of nonlinear effects in asymmetric synthesis. Adv. Synth. Catal., 343, 227-233.
    • (2001) Adv. Synth. Catal , vol.343 , pp. 227-233
    • Kagan, H.B.1
  • 29
    • 0033623873 scopus 로고    scopus 로고
    • Enantioselective auto-multiplication of chiral molecules by asymmetric catalysis
    • Soai, K., Shibata, T. and Sato, I. (2000) Enantioselective auto-multiplication of chiral molecules by asymmetric catalysis. Accounts Chem. Res., 33, 382-390.
    • (2000) Accounts Chem. Res , vol.33 , pp. 382-390
    • Soai, K.1    Shibata, T.2    Sato, I.3
  • 30
    • 0000906552 scopus 로고    scopus 로고
    • Nonlinear effects and autocatalysis
    • Jacobsen, E.N, Pfaltz, A and Yamamoto, H, eds, Springer-Verlag, Berlin
    • Kagan, H.B. and Luukas, T.O. (1999) Nonlinear effects and autocatalysis, in Comprehensive Asymmetric Catalysis, Jacobsen, E.N., Pfaltz, A and Yamamoto, H. (eds.), Springer-Verlag, Berlin, Vol. 1, pp. 101-118.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 101-118
    • Kagan, H.B.1    Luukas, T.O.2
  • 31
    • 2642647764 scopus 로고
    • The role of the product in asymmetric C-C bond formation: Stoichiometric and catalytic enatioselective autoinduction
    • Alberts, AH. and Wynberg, H. (1989) The role of the product in asymmetric C-C bond formation: stoichiometric and catalytic enatioselective autoinduction. J. Am. Chem. Soc., 111, 7265-7266.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 7265-7266
    • Alberts, A.H.1    Wynberg, H.2
  • 32
    • 0029742482 scopus 로고    scopus 로고
    • Asymmetric autocatalysis with amplification of chirality
    • and references quoted therein
    • (a) Bolm, C., Bienewald, F. and Seger, A. (1996) Asymmetric autocatalysis with amplification of chirality. Angew. Chem. Int. Edit. Engl., 35, 2922-2959 and references quoted therein.
    • (1996) Angew. Chem. Int. Edit. Engl , vol.35 , pp. 2922-2959
    • Bolm, C.1    Bienewald, F.2    Seger, A.3
  • 33
    • 20444456685 scopus 로고    scopus 로고
    • Dramatic catalyst evolution in the asymmetric addition of diethylzinc to benzaldehyde
    • and references quoted therein
    • (b) Costa, A.M, Garcia, C., Caroll, P.J. and Walsh, P.J. (2005) Dramatic catalyst evolution in the asymmetric addition of diethylzinc to benzaldehyde. Tetrahedron, 61, 6442-6446 and references quoted therein.
    • (2005) Tetrahedron , vol.61 , pp. 6442-6446
    • Costa, A.M.1    Garcia, C.2    Caroll, P.J.3    Walsh, P.J.4
  • 34
    • 0031593113 scopus 로고    scopus 로고
    • Mathematical models of nonlinear effects in asymmetric catalysis: New insights based on the role of reaction rate
    • Blackmond, D.G. (1997) Mathematical models of nonlinear effects in asymmetric catalysis: new insights based on the role of reaction rate. J. Am. Chem. Soc., 119, 12934-12939.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 12934-12939
    • Blackmond, D.G.1
  • 35
    • 0040514974 scopus 로고
    • Enantioselective addition of dialkylzincs to aldehydes promoted by chiral amino alcohols. Mechanism and nonlinear effect
    • Kitamura, M., Okada, S., Suga, S. and Noyori, R. (1989) Enantioselective addition of dialkylzincs to aldehydes promoted by chiral amino alcohols. Mechanism and nonlinear effect. J. Am. Chem. Soc., 111, 4028-4036.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 4028-4036
    • Kitamura, M.1    Okada, S.2    Suga, S.3    Noyori, R.4
  • 36
    • 33748247006 scopus 로고
    • Enantioselective addition of organometallic reagents to carbonyl compounds: Chirality transfer, multiplication, and amplification
    • Noyori, R. and Kitamura, L. (1991) Enantioselective addition of organometallic reagents to carbonyl compounds: chirality transfer, multiplication, and amplification. Angew. Chem. Int. Edit., 30, 49-69.
    • (1991) Angew. Chem. Int. Edit , vol.30 , pp. 49-69
    • Noyori, R.1    Kitamura, L.2
  • 37
    • 0000210159 scopus 로고
    • Asymmetric catalysis of Diels-Alder cycloadditions by an MS-free binaphthol-titanium complex: Dramatic effect of MS, linear vs. positive nonlinear relationship, and synthetic applications
    • Mikami, K., Motoyama, Y. and Terada, M. (1994) Asymmetric catalysis of Diels-Alder cycloadditions by an MS-free binaphthol-titanium complex: dramatic effect of MS, linear vs. positive nonlinear relationship, and synthetic applications. J. Am. Chem. Soc., 116, 2912-2820.
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 2912-2820
    • Mikami, K.1    Motoyama, Y.2    Terada, M.3
  • 38
    • 0001921539 scopus 로고
    • Characterization of the chiral titanium reagent prepared from the tartrate-derived chiral diol and titanium dichloride diisopropoxide
    • Iwasawa, N., Hayashi, Y., Sakurai, H. and Narasaka, K. (1989) Characterization of the chiral titanium reagent prepared from the tartrate-derived chiral diol and titanium dichloride diisopropoxide. Chem. Lett., 1581-1584.
    • (1989) Chem. Lett , pp. 1581-1584
    • Iwasawa, N.1    Hayashi, Y.2    Sakurai, H.3    Narasaka, K.4
  • 39
    • 0032495777 scopus 로고    scopus 로고
    • Transition-metal aqua complexes of 4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline). Effective catalysis in Diels-Alder reactions showing excellent enantioselectivity, extreme chiral amplification and high tolerance to water, alcohols, amines and acids
    • Kanemasa, S., Oderaotoshi, Y., Sakakguchi, S., Yamamoto, H., Tanaka, J., Wada, E. and Curran, D.P. (1998) Transition-metal aqua complexes of 4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline). Effective catalysis in Diels-Alder reactions showing excellent enantioselectivity, extreme chiral amplification and high tolerance to water, alcohols, amines and acids. J. Am. Chem. Soc., 120, 3074-3088.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 3074-3088
    • Kanemasa, S.1    Oderaotoshi, Y.2    Sakakguchi, S.3    Yamamoto, H.4    Tanaka, J.5    Wada, E.6    Curran, D.P.7
  • 40
    • 33645454196 scopus 로고    scopus 로고
    • A kinetic study on Rh/ Binap-catalyzed 14-addition of phenylboronic acid to enones: Negative nonlinear effect caused by predominant homochiral dimer contribution
    • Kina, A., Iwamura, H. and Hayashi, T. (2006) A kinetic study on Rh/ Binap-catalyzed 14-addition of phenylboronic acid to enones: negative nonlinear effect caused by predominant homochiral dimer contribution. J. Am. Chem. Soc., 128, 3904-3905.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 3904-3905
    • Kina, A.1    Iwamura, H.2    Hayashi, T.3
  • 41
    • 25444512653 scopus 로고    scopus 로고
    • Lewis acid-Lewis acid heterobimetallic cooperative catalysis: Mechanistic studies and application in enantioselective aza-Michael reaction
    • Yamagiwa N., Qin H., Matsunaga S. and Shibasaki M. (2005) Lewis acid-Lewis acid heterobimetallic cooperative catalysis: mechanistic studies and application in enantioselective aza-Michael reaction. J. Am. Chem. Soc., 127, 13419-13427.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 13419-13427
    • Yamagiwa, N.1    Qin, H.2    Matsunaga, S.3    Shibasaki, M.4
  • 42
    • 84989546359 scopus 로고
    • Asymmetric catalysis for carbonyl-ene reaction
    • Terada, M., Mikami, K. and Nakai, T. (1990) Asymmetric catalysis for carbonyl-ene reaction. Synlett, 255-264.
    • (1990) Synlett , pp. 255-264
    • Terada, M.1    Mikami, K.2    Nakai, T.3
  • 43
    • 0032749079 scopus 로고    scopus 로고
    • Non-linear effects in ruthenium-catalyzed asymmetric hydrogenation with atropisomeric diphosphanes
    • Girard, C., Genet, J.-P. and Buillard, M. (1999) Non-linear effects in ruthenium-catalyzed asymmetric hydrogenation with atropisomeric diphosphanes. Eur. J. Org. Chem., 11, 2937-2942.
    • (1999) Eur. J. Org. Chem , vol.11 , pp. 2937-2942
    • Girard, C.1    Genet, J.-P.2    Buillard, M.3
  • 44
  • 45
    • 0032486159 scopus 로고    scopus 로고
    • Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts
    • Brunel, J.-M., Luukas, T.O. and Kagan, H.B. (1998) Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron-Asymmetr., 9, 1941-1946.
    • (1998) Tetrahedron-Asymmetr , vol.9 , pp. 1941-1946
    • Brunel, J.-M.1    Luukas, T.O.2    Kagan, H.B.3
  • 46
    • 0029798420 scopus 로고    scopus 로고
    • III complexes. J. Am. Chem. Soc., 118, 10924-10925.
    • III complexes. J. Am. Chem. Soc., 118, 10924-10925.
  • 47
    • 0000670716 scopus 로고
    • Nouvelle méthode pour porter au maximum la pureté optique d'un produit partiellement dédoublé sans l'aide d'aucune substance chirale.
    • Vigneron, J.-P., Dhaenens, M. and Horeau, A. (1973) Nouvelle méthode pour porter au maximum la pureté optique d'un produit partiellement dédoublé sans l'aide d'aucune substance chirale. Tetrahedron, 29, 1055-1059.
    • (1973) Tetrahedron , vol.29 , pp. 1055-1059
    • Vigneron, J.-P.1    Dhaenens, M.2    Horeau, A.3
  • 48
    • 0004769513 scopus 로고
    • Theories of the origin and maintenance of optical activity in nature
    • (a) Langenbeck, W. and Triem, G. (1936) Theories of the origin and maintenance of optical activity in nature. Z. Phys. Chem. A, 177, 401-409.
    • (1936) Z. Phys. Chem. A , vol.177 , pp. 401-409
    • Langenbeck, W.1    Triem, G.2
  • 50
    • 0034680593 scopus 로고    scopus 로고
    • New developments in the origin of the homochirality of biologically relevant molecules
    • Buschmann, H., Thede, R. and Heller, D. (2000) New developments in the origin of the homochirality of biologically relevant molecules. Angew. Chem. Int. Edit., 39, 4033-4036.
    • (2000) Angew. Chem. Int. Edit , vol.39 , pp. 4033-4036
    • Buschmann, H.1    Thede, R.2    Heller, D.3


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