메뉴 건너뛰기




Volumn 33, Issue 6, 2000, Pages 432-440

Asymmetric catalysis of aldol reactions with chiral Lewis bases

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; BASE; KETONE; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDIC ACID DERIVATIVE; SILANE DERIVATIVE;

EID: 0033935920     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960027g     Document Type: Article
Times cited : (353)

References (59)
  • 5
    • 0000892247 scopus 로고    scopus 로고
    • The catalyzed α-hydroxyalkyl-ation and α-aminoalkylation of activated olefins (the Morita-Baylis-Hillman reaction)
    • (b) Ciganek, E. The Catalyzed α-Hydroxyalkyl-ation and α-Aminoalkylation of Activated Olefins (The Morita-Baylis-Hillman Reaction). Org. React. 1997, 51, 201-350.
    • (1997) Org. React. , vol.51 , pp. 201-350
    • Ciganek, E.1
  • 6
    • 0342714136 scopus 로고    scopus 로고
    • manuscript in preparation for submission to
    • An in-depth discussion of this concept and its consequences for chemical reactivity will be the subjects of a forthcoming review: Denmark, S. E.; Stavenger, R. A., manuscript in preparation for submission to Angew. Chem., Int. Ed.
    • Angew. Chem., Int. Ed.
    • Denmark, S.E.1    Stavenger, R.A.2
  • 7
    • 0001214450 scopus 로고
    • Reactivity of penta- and hexacoordinate silicon compounds and their role as reaction intermediates
    • Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Reactivity of Penta- and Hexacoordinate Silicon Compounds and Their Role as Reaction Intermediates. Chem. Rev. 1993, 93, 1371-1448.
    • (1993) Chem. Rev. , vol.93 , pp. 1371-1448
    • Chuit, C.1    Corriu, R.J.P.2    Reye, C.3    Young, J.C.4
  • 8
    • 0003914496 scopus 로고    scopus 로고
    • Stable diaqua palladium(II) complexes of BINAP and tol-BINAP as highly efficient catalysts for asymmetric aldol reactions
    • For examples of a recently developed, third class of aldol addition that involves the use of chirally modified metalloids in a catalytic process, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Stable Diaqua Palladium(II) Complexes of BINAP and Tol-BINAP as Highly Efficient Catalysts for Asymmetric Aldol Reactions. Synlett 1997, 463-466.
    • (1997) Synlett , pp. 463-466
    • Sodeoka, M.1    Tokunoh, R.2    Miyazaki, F.3    Hagiwara, E.4    Shibasaki, M.5
  • 9
    • 0030827816 scopus 로고    scopus 로고
    • Enantioselective aldol reaction of tin enolates with aldehydes catalyzed by BINAP-silver(I) complex
    • (b) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. Enantioselective Aldol Reaction of Tin Enolates with Aldehydes Catalyzed by BINAP-Silver(I) Complex. J. Am. Chem. Soc. 1997, 119, 9319-9320.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9319-9320
    • Yanagisawa, A.1    Matsumoto, Y.2    Nakashima, H.3    Asakawa, K.4    Yamamoto, H.5
  • 10
    • 0038475549 scopus 로고    scopus 로고
    • Apparent catalytic generation of chiral metal enolates: Enantioselective dienolate additions to aldehydes mediated by tol-BINAP-Cu(II) fluoride complexes
    • (c) Krüger, J.; Carreira, E. M. Apparent Catalytic Generation of Chiral Metal Enolates: Enantioselective Dienolate Additions to Aldehydes Mediated by Tol-BINAP-Cu(II) Fluoride Complexes. J. Am. Chem. Soc 1998, 120, 837-838.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 837-838
    • Krüger, J.1    Carreira, E.M.2
  • 11
    • 0001924338 scopus 로고
    • Stereoselective aldol condensations
    • Eliel, E. L., Wilen, S. H., Eds.; Wiley-Interscience: New York
    • (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Stereoselective Aldol Condensations. In Topics in Stereochemistry, Eliel, E. L., Wilen, S. H., Eds.; Wiley-Interscience: New York, 1982; Vol. 13, pp 1-116.
    • (1982) Topics in Stereochemistry , vol.13 , pp. 1-116
    • Evans, D.A.1    Nelson, J.V.2    Taber, T.R.3
  • 12
    • 0000584420 scopus 로고
    • The aldol addition reaction
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 2
    • (b) Heathcock, C. H. The Aldol Addition Reaction. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2, pp 111-212.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 111-212
    • Heathcock, C.H.1
  • 13
    • 84973329202 scopus 로고
    • Stereoselective aldol reactions with α-unsubstituted chiral enolates
    • (c) Braun, M. Stereoselective Aldol Reactions with α-Unsubstituted Chiral Enolates. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37.
    • (1987) Angew. Chem., Int. Ed. Engl. , vol.26 , pp. 24-37
    • Braun, M.1
  • 15
    • 0001653533 scopus 로고
    • The aldol reaction: Transition metal enolates
    • Heathcock, C. H., Ed.; Pergamon Press: Oxford, Chapter 1.9
    • (e) Paterson, I. The Aldol Reaction: Transition Metal Enolates. In Comprehesive Organic Synthesis: Additions to C-X π-Bonds Part 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Chapter 1.9, pp 301 -320.
    • (1991) Comprehesive Organic Synthesis: Additions to C-X π-Bonds Part 2 , pp. 301-320
    • Paterson, I.1
  • 16
    • 0001316868 scopus 로고
    • Asymmetric synthesis with enol ethers
    • Heathcock, C. H., Ed.; Pergamon Press: Oxford, Chapter 2.4
    • (f) Gennari, C. Asymmetric Synthesis with Enol Ethers. In Comprehesive Organic Synthesis: Additions to C-X π-Bonus Part 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Chapter 2.4, pp 629-660.
    • (1991) Comprehesive Organic Synthesis: Additions to C-X π-Bonus Part 2 , pp. 629-660
    • Gennari, C.1
  • 17
    • 0002384398 scopus 로고
    • Tin(II) enolates in the aldol, michael, and related reactions
    • (g) Mukaiyama, T.; Kobayashi, S. Tin(II) Enolates in the Aldol, Michael, and Related Reactions. Org. React. 1994, 46, 1-103.
    • (1994) Org. React. , vol.46 , pp. 1-103
    • Mukaiyama, T.1    Kobayashi, S.2
  • 18
    • 0001790298 scopus 로고    scopus 로고
    • Asymmetric aldol reactions using boron enolates
    • (h) Cowden, C. J.; Paterson, I. Asymmetric Aldol Reactions Using Boron Enolates. Org. React. 1997, 57, 1-200.
    • (1997) Org. React. , vol.57 , pp. 1-200
    • Cowden, C.J.1    Paterson, I.2
  • 19
    • 0000922736 scopus 로고    scopus 로고
    • Simple diastereoselection and transition state models
    • Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart
    • (i) Braun, M. Simple Diastereoselection and Transition State Models. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, pp 1603-1666.
    • (1996) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21 , vol.3 , pp. 1603-1666
    • Braun, M.1
  • 21
    • 0000699983 scopus 로고    scopus 로고
    • Mukaiyama aldol reaction
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Chapter 29.1
    • For excellent reviews, see: (a) Carreira, E. M. Mukaiyama Aldol Reaction. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. III, Chapter 29.1.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Carreira, E.M.1
  • 22
    • 0000312386 scopus 로고    scopus 로고
    • Addition of achiral enolates to achiral carbonyl compunds in the presence of chiral additives and catalysts
    • Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart
    • (b) Braun, M. Addition of Achiral Enolates to Achiral Carbonyl Compunds in the Presence of Chiral Additives and Catalysts. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, pp 1730-1736.
    • (1996) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21 , vol.3 , pp. 1730-1736
    • Braun, M.1
  • 23
    • 0032512595 scopus 로고    scopus 로고
    • Catalyzed enantioselective aldol additions of latent enolate equivalents
    • (c) Nelson, S. G. Catalyzed Enantioselective Aldol Additions of Latent Enolate Equivalents. Tetrahedron: Asymmetry 1998, 9, 357-389.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 357-389
    • Nelson, S.G.1
  • 28
    • 0343148624 scopus 로고
    • O- and C-organometallic isomers. VI. O-organometallic (silicon, germanium, tin, boron) derivatives of cyclohexen-1-ol
    • (c) Ponomarev, S. V.; Baukov, Y. I.; Dudukina, O. V.; Petrosyan, I. V.; Petrovskaya, L. I. O- and C-Organometallic Isomers. VI. O-Organometallic (Silicon, Germanium, Tin, Boron) Derivatives of Cyclohexen-1-ol. Zh. Obshch. Khim. 1967, 37, 2204-2207.
    • (1967) Zh. Obshch. Khim. , vol.37 , pp. 2204-2207
    • Ponomarev, S.V.1    Baukov, Y.I.2    Dudukina, O.V.3    Petrosyan, I.V.4    Petrovskaya, L.I.5
  • 29
    • 0001503612 scopus 로고
    • Trichlorosilane-tertiary amine combinations as reducing agents for polyhalo compounds. Potential analogies with phosphorus chemistry
    • (d) Benkeser, R. A.; Smith, W. E. Trichlorosilane-Tertiary Amine Combinations as Reducing Agents for Polyhalo Compounds. Potential Analogies with Phosphorus Chemistry. J. Am. Chem. Soc. 1968, 90, 5307-5309.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5307-5309
    • Benkeser, R.A.1    Smith, W.E.2
  • 30
    • 0343584236 scopus 로고    scopus 로고
    • note
    • HMPA and related phosphoramides are known to have the highest donicities of common solvents, see: (a) Reference 11.
  • 31
    • 0004903668 scopus 로고
    • Gibbs energies, entropies and enthalpies of transfer for divalent cations to several solvents
    • (b) Gritzner, G.; Hörzenberger, F. Gibbs Energies, Entropies and Enthalpies of Transfer for Divalent Cations to Several Solvents. J. Chem. Soc., Faraday Trans. 1995, 91, 3843-3850.
    • (1995) J. Chem. Soc., Faraday Trans. , vol.91 , pp. 3843-3850
    • Gritzner, G.1    Hörzenberger, F.2
  • 32
    • 84945017431 scopus 로고
    • The softness parameter (SP), a measure of the soft donor properties of solvents
    • (c) Gritzner, G. The Softness Parameter (SP), a Measure of the Soft Donor Properties of Solvents. Z. Phys. Chem. Neue Folge 1988, 158, 99-107.
    • (1988) Z. Phys. Chem. Neue Folge , vol.158 , pp. 99-107
    • Gritzner, G.1
  • 33
    • 0000239256 scopus 로고    scopus 로고
    • A critical view on the Lewis donor (Nucleophilic) properties of solvents
    • (d) Gritzner, G. A Critical View on the Lewis Donor (Nucleophilic) Properties of Solvents. J. Mol. Liq. 1997, 487-500.
    • (1997) J. Mol. Liq. , pp. 487-500
    • Gritzner, G.1
  • 34
    • 0000455687 scopus 로고
    • 3, Br, CI) with nucleophiles. The nature of silylation mixtures in solution
    • 3, Br, CI) with Nucleophiles. The Nature of Silylation Mixtures in Solution. Tetrahedron Lett. 1985, 26, 3403-3406.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 3403-3406
    • Bassindale, A.R.1    Stout, T.2
  • 35
    • 0000444566 scopus 로고
    • Kinetics of the reactions of allylsilanes, allylgermanes, and allylstannanes with carbenium ions
    • Hagan, G.; Mayr, H. Kinetics of the Reactions of Allylsilanes, Allylgermanes, and Allylstannanes with Carbenium Ions. J. Am. Chem. Soc. 1991, 113, 4954-4961.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4954-4961
    • Hagan, G.1    Mayr, H.2
  • 36
    • 0029764219 scopus 로고    scopus 로고
    • Chemistry of trichlorosilyl enolates. 1. New reagents for catalytic, asymmetric aldol additions
    • Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. Chemistry of Trichlorosilyl Enolates. 1. New Reagents for Catalytic, Asymmetric Aldol Additions. J. Am. Chem. Soc. 1996, 118, 7404-7405.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7404-7405
    • Denmark, S.E.1    Winter, S.B.D.2    Su, X.3    Wong, K.-T.4
  • 37
    • 0033583164 scopus 로고    scopus 로고
    • Synthesis of phosphoramides for the Lewis base-catalyzed allylation and aldol addition reactions
    • Denmark, S. E.; Su, X.; Nishigaichi, Y.; Coe, D. M.; Wong, K.-T.; Winter, S. B. D.; Choi, J. Y. Synthesis of Phosphoramides for the Lewis Base-Catalyzed Allylation and Aldol Addition Reactions. J. Org. Chem. 1999, 64, 1958-1967.
    • (1999) J. Org. Chem. , vol.64 , pp. 1958-1967
    • Denmark, S.E.1    Su, X.2    Nishigaichi, Y.3    Coe, D.M.4    Wong, K.-T.5    Winter, S.B.D.6    Choi, J.Y.7
  • 38
    • 1542525127 scopus 로고    scopus 로고
    • The chemistry of chlorosilyl enolates. Variation of the silyl group and the effect on rate and enantiomeric excess of acetate aldol additions
    • Denmark, S. E.; Winter, S. B. D. The Chemistry of Chlorosilyl Enolates. Variation of the Silyl Group and the Effect on Rate and Enantiomeric Excess of Acetate Aldol Additions. Synlett 1997, 1087-1089.
    • (1997) Synlett , pp. 1087-1089
    • Denmark, S.E.1    Winter, S.B.D.2
  • 39
    • 0039353913 scopus 로고
    • Hypervalent silicon compounds
    • Patai, S., Rappoport, Z., Eds.; Wiley: New York, Chapter 1
    • Corriu, R. J. P.; Young, J. C. Hypervalent Silicon Compounds. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Chapter 1, pp 1-48.
    • (1991) The Silicon-Heteroatom Bond , pp. 1-48
    • Corriu, R.J.P.1    Young, J.C.2
  • 40
    • 0001126230 scopus 로고    scopus 로고
    • Lewis base-catalyzed, asymmetric aldol additions of methyl ketone enolates
    • Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. Lewis Base-Catalyzed, Asymmetric Aldol Additions of Methyl Ketone Enolates. J. Org. Chem. 1998, 63, 918-919.
    • (1998) J. Org. Chem. , vol.63 , pp. 918-919
    • Denmark, S.E.1    Stavenger, R.A.2    Wong, K.-T.3
  • 41
    • 0032509556 scopus 로고    scopus 로고
    • Highly 1,4-syn diastereoselective, phosphoramide-catalyzed aldol additions of chiral methyl ketone enolates
    • Denmark, S. E.; Stavenger, R. A. Highly 1,4-syn Diastereoselective, Phosphoramide-Catalyzed Aldol Additions of Chiral Methyl Ketone Enolates. J. Org. Chem. 1998, 63, 9524-9527.
    • (1998) J. Org. Chem. , vol.63 , pp. 9524-9527
    • Denmark, S.E.1    Stavenger, R.A.2
  • 42
    • 0030933807 scopus 로고    scopus 로고
    • The chemistry of trichlorosilyl enolates. 2. Highly-selective asymmetric aldol additions of ketone enolates
    • (a) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. The Chemistry of Trichlorosilyl Enolates. 2. Highly-Selective Asymmetric Aldol Additions of Ketone Enolates. J. Am. Chem. Soc. 1997, 119, 2333-2334.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2333-2334
    • Denmark, S.E.1    Wong, K.-T.2    Stavenger, R.A.3
  • 43
    • 0033516307 scopus 로고    scopus 로고
    • Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects
    • (b) Denmark, S. E.; Stavenger, R. A.; Wong, K. T.; Su, X. Chiral Phosphoramide-Catalyzed Aldol Additions of Ketone Enolates. Preparative Aspects. J. Am. Chem. Soc. 1999, 121, 4982-4991.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4982-4991
    • Denmark, S.E.1    Stavenger, R.A.2    Wong, K.T.3    Su, X.4
  • 45
    • 0032572895 scopus 로고    scopus 로고
    • Asymmetric aldol additions catalyzed by chiral phosphoramides: Electronic effects of the aldehyde component
    • Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. Asymmetric Aldol Additions Catalyzed by Chiral Phosphoramides: Electronic Effects of the Aldehyde Component. Tetrahedron 1998, 54, 10389-10402.
    • (1998) Tetrahedron , vol.54 , pp. 10389-10402
    • Denmark, S.E.1    Stavenger, R.A.2    Wong, K.-T.3
  • 46
    • 0032539228 scopus 로고    scopus 로고
    • The chemistry of trichlorosilyl enolates. 6. Mechanistic duality in the Lewis base-catalyzed aldol addition reaction
    • Denmark, S. E.; Su, X.; Nishigaichi, Y. The Chemistry of Trichlorosilyl Enolates. 6. Mechanistic Duality in the Lewis Base-Catalyzed Aldol Addition Reaction. J. Am. Chem. Soc. 1998, 120, 12990-12991.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 12990-12991
    • Denmark, S.E.1    Su, X.2    Nishigaichi, Y.3
  • 48
    • 0000025972 scopus 로고    scopus 로고
    • Asymmetric amplification
    • (b) Kagan, H. B.; Fenwick, D. Asymmetric Amplification. Top. Stereochem. 1999, 22, 257-296.
    • (1999) Top. Stereochem. , vol.22 , pp. 257-296
    • Kagan, H.B.1    Fenwick, D.2
  • 50
    • 0342714121 scopus 로고    scopus 로고
    • Kinetic analysis of chiral Lewis base catalyzed aldol additions of trichlorosilyl enol ethers: A rapid injection NMR study
    • Manuscript submitted to
    • Denmark, S. E.; Pham, S. M., Kinetic Analysis of Chiral Lewis Base Catalyzed Aldol Additions of Trichlorosilyl Enol Ethers: A Rapid Injection NMR Study. Manuscript submitted to Helv. Chim. Acta.
    • Helv. Chim. Acta
    • Denmark, S.E.1    Pham, S.M.2
  • 52
    • 84986848006 scopus 로고
    • Rapid injection NMR: A simple technique for the observation of reactive intermediates
    • For examples on the use of rapid injection NMR techniques, see: (a) McGarrity, J. F.; Prodolliet, J.; Smyth, T. Rapid Injection NMR: A Simple Technique for the Observation of Reactive Intermediates. Org. Magn. Reson. 1981, 17, 59-65.
    • (1981) Org. Magn. Reson. , vol.17 , pp. 59-65
    • McGarrity, J.F.1    Prodolliet, J.2    Smyth, T.3
  • 53
    • 0000289680 scopus 로고
    • Mechanistic studies on the base-promoted addition of lithiumpinacolonate to several aromatic carbonyl compounds in nonhydroxylic solvents
    • (b) Palmer, C. A.; Ogle, C. A.; Arnett, E. M. Mechanistic Studies on the Base-Promoted Addition of Lithiumpinacolonate to Several Aromatic Carbonyl Compounds in Nonhydroxylic Solvents. J. Am. Chem. Soc. 1992, 114, 5619-5625.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5619-5625
    • Palmer, C.A.1    Ogle, C.A.2    Arnett, E.M.3
  • 55
    • 0343584232 scopus 로고    scopus 로고
    • note
    • The importance of the ordering of the subsequent steps is at present unknown.
  • 56
    • 0033575491 scopus 로고    scopus 로고
    • Solid state and solution structural studies of chiral phosphoramide-tin complexes relevant to Lewis base-catalyzed aldol reactions
    • Denmark, S. E.; Su, X. Solid State and Solution Structural Studies of Chiral Phosphoramide-Tin Complexes Relevant to Lewis Base-Catalyzed Aldol Reactions. Tetrahedron 1999, 55, 8727-8738. Attempts to identify stable complexes with silicon(IV) Lewis acids were not productive.
    • (1999) Tetrahedron , vol.55 , pp. 8727-8738
    • Denmark, S.E.1    Su, X.2
  • 57
    • 0342714118 scopus 로고    scopus 로고
    • unpublished studies from these laboratories
    • Such tethering of phosphoramides has given rise to highly selective and efficient catalysts for enantioselective allylation. Fu, J. unpublished studies from these laboratories.
    • Fu, J.1
  • 58
    • 33751157465 scopus 로고
    • Asymmetric allylation of aldehydes with chiral Lewis bases
    • Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. Asymmetric Allylation of Aldehydes with Chiral Lewis Bases. J. Org. Chem. 1994, 59, 6161-6163.
    • (1994) J. Org. Chem. , vol.59 , pp. 6161-6163
    • Denmark, S.E.1    Coe, D.M.2    Pratt, N.E.3    Griedel, B.D.4
  • 59
    • 0000048225 scopus 로고    scopus 로고
    • Enantioselective ring opening of epoxides with silicon tetrachloride in the presence of a chiral Lewis base
    • Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. Enantioselective Ring Opening of Epoxides with Silicon Tetrachloride in the Presence of a Chiral Lewis Base. J. Org. Chem. 1998, 63, 2428-2429.
    • (1998) J. Org. Chem. , vol.63 , pp. 2428-2429
    • Denmark, S.E.1    Barsanti, P.A.2    Wong, K.-T.3    Stavenger, R.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.