메뉴 건너뛰기




Volumn 14, Issue 3, 2010, Pages 371-382

Recent advances in multicomponent reactions for diversity-oriented synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALDEHYDE; AMINE; BORONIC ACID DERIVATIVE; CARBOXYLIC ACID; ISONITRILE DERIVATIVE; OXINDOLE; SPRIOOXINDOLE; UNCLASSIFIED DRUG;

EID: 77952542304     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2010.03.003     Document Type: Review
Times cited : (489)

References (87)
  • 1
    • 84890597202 scopus 로고    scopus 로고
    • Zhu J., and Bienayme H. (Eds)
    • In: Zhu J., and Bienayme H. (Eds). Multicomponent Reactions (2005)
    • (2005) Multicomponent Reactions
  • 2
    • 0033019939 scopus 로고    scopus 로고
    • Discovery of new multi component reactions with combinatorial methods
    • "True multicomponent reactions should be distinguished from the so-called tandem, cascade, domino or zipper reactions where one starting material bears with several functionalities that react in several consecutive steps, whereas 'pure' MCRs are run under the same conditions by adding the starting materials at the same time."
    • Weber L., Illgen K., and Almstetter M. Discovery of new multi component reactions with combinatorial methods. Synlett (1999) 366-374. "True multicomponent reactions should be distinguished from the so-called tandem, cascade, domino or zipper reactions where one starting material bears with several functionalities that react in several consecutive steps, whereas 'pure' MCRs are run under the same conditions by adding the starting materials at the same time."
    • (1999) Synlett , pp. 366-374
    • Weber, L.1    Illgen, K.2    Almstetter, M.3
  • 3
    • 31544434530 scopus 로고    scopus 로고
    • Recent developments in isocyanide based multicomponent reactions in applied chemistry
    • Doemling A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106 (2006) 17-89
    • (2006) Chem Rev , vol.106 , pp. 17-89
    • Doemling, A.1
  • 4
    • 32344433949 scopus 로고    scopus 로고
    • Elsevier Academic Press, Burlington, MA. This book contains concise histories, mechanisms, and examples of synthetic utility for a wide variety of named reactions, including many MCRs.
    • Kürti L., and Czakó B. Strategic Applications of Named Reactions in Organic Synthesis (2005), Elsevier Academic Press, Burlington, MA. This book contains concise histories, mechanisms, and examples of synthetic utility for a wide variety of named reactions, including many MCRs.
    • (2005) Strategic Applications of Named Reactions in Organic Synthesis
    • Kürti, L.1    Czakó, B.2
  • 5
    • 69649109186 scopus 로고    scopus 로고
    • The academic pursuit of screening
    • The academic pursuit of screening. Nat Chem Biol 3 (2007) 433
    • (2007) Nat Chem Biol , vol.3 , pp. 433
  • 6
    • 70349156384 scopus 로고    scopus 로고
    • Natural product synthesis using multicomponent reaction strategies
    • Touré B.B., and Hall D.G. Natural product synthesis using multicomponent reaction strategies. Chem Rev 109 (2009) 4439-4486
    • (2009) Chem Rev , vol.109 , pp. 4439-4486
    • Touré, B.B.1    Hall, D.G.2
  • 7
    • 33746897660 scopus 로고    scopus 로고
    • Design and synthesis of new classes of heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs)
    • Dondoni A., and Massi A. Design and synthesis of new classes of heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs). Acc Chem Res 39 (2006) 451-463
    • (2006) Acc Chem Res , vol.39 , pp. 451-463
    • Dondoni, A.1    Massi, A.2
  • 8
    • 63849191356 scopus 로고    scopus 로고
    • Multiple multicomponent macrocyclizations (MiBs): a strategic development toward macrocycle diversity
    • Wessjohann L.A., Rivera D.G., and Vercillo O.E. Multiple multicomponent macrocyclizations (MiBs): a strategic development toward macrocycle diversity. Chem Rev 109 (2009) 796-814
    • (2009) Chem Rev , vol.109 , pp. 796-814
    • Wessjohann, L.A.1    Rivera, D.G.2    Vercillo, O.E.3
  • 9
    • 77952544352 scopus 로고    scopus 로고
    • Claims regarding the 'first' catalysts refer to the use of chemical entities other than simple protic acids. These claims are made based on a thorough perusal of the literature and with the input of experts in the field (see Acknowledgements). References are included in the sections below that discuss the individual reactions. Readers are encouraged to contact JTS to point out any instance in which earlier examples are documented.
    • Claims regarding the 'first' catalysts refer to the use of chemical entities other than simple protic acids. These claims are made based on a thorough perusal of the literature and with the input of experts in the field (see Acknowledgements). References are included in the sections below that discuss the individual reactions. Readers are encouraged to contact JTS to point out any instance in which earlier examples are documented.
  • 10
    • 17144366282 scopus 로고    scopus 로고
    • Asymmetric multicomponent reactions (AMCRs): the new frontier
    • Ramon D.J., and Yus M. Asymmetric multicomponent reactions (AMCRs): the new frontier. Angew Chem Int Ed 44 (2005) 1602-1634
    • (2005) Angew Chem Int Ed , vol.44 , pp. 1602-1634
    • Ramon, D.J.1    Yus, M.2
  • 11
    • 37549020046 scopus 로고    scopus 로고
    • Towards the optimal screening collection. A synthesis strategy
    • This review discussed many recent examples of diversity-oriented synthesis (DOS) in which MCRs play key synthetic roles.
    • Nielsen T.E., and Schreiber S.L. Towards the optimal screening collection. A synthesis strategy. Angew Chem Int Ed 47 (2008) 48-56. This review discussed many recent examples of diversity-oriented synthesis (DOS) in which MCRs play key synthetic roles.
    • (2008) Angew Chem Int Ed , vol.47 , pp. 48-56
    • Nielsen, T.E.1    Schreiber, S.L.2
  • 12
    • 58149358949 scopus 로고    scopus 로고
    • Molecular diversity by design
    • Schreiber S.L. Molecular diversity by design. Nature (London, UK) 457 (2009) 153-154
    • (2009) Nature (London, UK) , vol.457 , pp. 153-154
    • Schreiber, S.L.1
  • 13
    • 11144310072 scopus 로고    scopus 로고
    • Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions
    • Simon C., Constantieux T., and Rodriguez J. Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions. Eur J Org Chem (2004) 4957-4980
    • (2004) Eur J Org Chem , pp. 4957-4980
    • Simon, C.1    Constantieux, T.2    Rodriguez, J.3
  • 15
    • 41049106516 scopus 로고    scopus 로고
    • One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid catalyzed Hantzsch three-component reaction
    • Debache A., Boulcina R., Belfaitah A., Rhouati S., and Carboni B. One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid catalyzed Hantzsch three-component reaction. Synlett (2008) 509-512
    • (2008) Synlett , pp. 509-512
    • Debache, A.1    Boulcina, R.2    Belfaitah, A.3    Rhouati, S.4    Carboni, B.5
  • 16
    • 33846336715 scopus 로고    scopus 로고
    • Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts
    • Kumar A., and Maurya R.A. Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts. Tetrahedron 63 (2007) 1946-1952
    • (2007) Tetrahedron , vol.63 , pp. 1946-1952
    • Kumar, A.1    Maurya, R.A.2
  • 17
    • 33745216463 scopus 로고    scopus 로고
    • Ceric ammonium nitrate (CAN) catalyzes the one-pot synthesis of polyhydroquinoline via the Hantzsch reaction
    • Ko S., and Yao C.-F. Ceric ammonium nitrate (CAN) catalyzes the one-pot synthesis of polyhydroquinoline via the Hantzsch reaction. Tetrahedron 62 (2006) 7293-7299
    • (2006) Tetrahedron , vol.62 , pp. 7293-7299
    • Ko, S.1    Yao, C.-F.2
  • 18
    • 67650286836 scopus 로고    scopus 로고
    • Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines
    • Evans C.G., and Gestwicki J.E. Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines. Org Lett 11 (2009) 2957-2959
    • (2009) Org Lett , vol.11 , pp. 2957-2959
    • Evans, C.G.1    Gestwicki, J.E.2
  • 19
    • 70349590524 scopus 로고    scopus 로고
    • A four-component, one-pot synthesis of highly substituted 1,4-dihydro-1,8-naphthyridine-3-carboxamides
    • Shaabani A., Seyyedhamzeh M., Maleki A., and Behnam M. A four-component, one-pot synthesis of highly substituted 1,4-dihydro-1,8-naphthyridine-3-carboxamides. Tetrahedron Lett 50 (2009) 6355-6357
    • (2009) Tetrahedron Lett , vol.50 , pp. 6355-6357
    • Shaabani, A.1    Seyyedhamzeh, M.2    Maleki, A.3    Behnam, M.4
  • 20
    • 40849097396 scopus 로고    scopus 로고
    • Multicomponent reactions for the synthesis of new 3′-indolyl substituted heterocycles under microwave irradiation
    • Zhu S.-L., Ji S.-J., Zhao K., and Liu Y. Multicomponent reactions for the synthesis of new 3′-indolyl substituted heterocycles under microwave irradiation. Tetrahedron Lett 49 (2008) 2578-2582
    • (2008) Tetrahedron Lett , vol.49 , pp. 2578-2582
    • Zhu, S.-L.1    Ji, S.-J.2    Zhao, K.3    Liu, Y.4
  • 21
    • 54049096626 scopus 로고    scopus 로고
    • One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives
    • Bazgir A., Khanaposhtani M.M., and Soorki A.A. One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives. Bioorg Med Chem Lett 18 (2008) 5800-5803
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 5800-5803
    • Bazgir, A.1    Khanaposhtani, M.M.2    Soorki, A.A.3
  • 24
    • 0038512037 scopus 로고    scopus 로고
    • Molecular shape diversity of combinatorial libraries: a prerequisite for broad bioactivity
    • This article describes a simple method for quantifying and graphically depicting the variation in three-dimensional shape of a collection of compounds by considering three limiting cases: rods, disks, and spheres.
    • Sauer W.H.B., and Schwarz M.K. Molecular shape diversity of combinatorial libraries: a prerequisite for broad bioactivity. J Chem Inf Comput Sci 43 (2003) 987-1003. This article describes a simple method for quantifying and graphically depicting the variation in three-dimensional shape of a collection of compounds by considering three limiting cases: rods, disks, and spheres.
    • (2003) J Chem Inf Comput Sci , vol.43 , pp. 987-1003
    • Sauer, W.H.B.1    Schwarz, M.K.2
  • 25
    • 67650680895 scopus 로고    scopus 로고
    • Highly diastereoselective domino synthesis of 6-spirosubstituted pyrido[2,3-d]pyrimidine derivatives in water
    • Jiang B., Cao L.-J., Tu S.-J., Zheng W.-R., and Yu H.-Z. Highly diastereoselective domino synthesis of 6-spirosubstituted pyrido[2,3-d]pyrimidine derivatives in water. J Comb Chem 11 (2009) 612-616
    • (2009) J Comb Chem , vol.11 , pp. 612-616
    • Jiang, B.1    Cao, L.-J.2    Tu, S.-J.3    Zheng, W.-R.4    Yu, H.-Z.5
  • 26
    • 34247096074 scopus 로고    scopus 로고
    • A new three-component domino synthesis of 1,4-dihydropyridines
    • Sridharan V., Perumal P.T., Avendaño C., and Menéndez J.C. A new three-component domino synthesis of 1,4-dihydropyridines. Tetrahedron 63 (2007) 4407-4413
    • (2007) Tetrahedron , vol.63 , pp. 4407-4413
    • Sridharan, V.1    Perumal, P.T.2    Avendaño, C.3    Menéndez, J.C.4
  • 27
    • 65349107107 scopus 로고    scopus 로고
    • A very efficient cerium(IV) ammonium nitrate catalyzed, four-component synthesis of tetrahydropyridines and its application in the concise generation of functionalized homoquinolizine frameworks
    • Sridharan V., Maiti S., and Menendez J.C. A very efficient cerium(IV) ammonium nitrate catalyzed, four-component synthesis of tetrahydropyridines and its application in the concise generation of functionalized homoquinolizine frameworks. Chem Eur J 15 (2009) 4565-4572
    • (2009) Chem Eur J , vol.15 , pp. 4565-4572
    • Sridharan, V.1    Maiti, S.2    Menendez, J.C.3
  • 28
    • 46649090552 scopus 로고    scopus 로고
    • Convenient one-pot synthesis of chiral tetrahydropyridines via a multicomponent reaction
    • Noel R., Fargeau-Bellassoued M.-C., Vanucci-Bacque C., and Lhommet G. Convenient one-pot synthesis of chiral tetrahydropyridines via a multicomponent reaction. Synthesis (2008) 1948-1954
    • (2008) Synthesis , pp. 1948-1954
    • Noel, R.1    Fargeau-Bellassoued, M.-C.2    Vanucci-Bacque, C.3    Lhommet, G.4
  • 29
    • 0034518876 scopus 로고    scopus 로고
    • Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog
    • Kappe C.O. Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc Chem Res 33 (2000) 879-888
    • (2000) Acc Chem Res , vol.33 , pp. 879-888
    • Kappe, C.O.1
  • 30
    • 3242728210 scopus 로고    scopus 로고
    • The Biginelli dihydropyrimidinone synthesis
    • Kappe C.O., and Stadler A. The Biginelli dihydropyrimidinone synthesis. Org React (New York) 63 (2004) 1-116
    • (2004) Org React (New York) , vol.63 , pp. 1-116
    • Kappe, C.O.1    Stadler, A.2
  • 31
    • 0000685535 scopus 로고
    • Studies toward the total synthesis of (+)-ptilomycalin A. Use of a tethered Biginelli condensation for the preparation of an advanced tricyclic intermediate
    • Overman L.E., and Rabinowitz M.H. Studies toward the total synthesis of (+)-ptilomycalin A. Use of a tethered Biginelli condensation for the preparation of an advanced tricyclic intermediate. J Org Chem 58 (1993) 3235-3237
    • (1993) J Org Chem , vol.58 , pp. 3235-3237
    • Overman, L.E.1    Rabinowitz, M.H.2
  • 32
    • 0028939869 scopus 로고
    • Enantioselective total synthesis of (-)-ptilomycalin A
    • Overman L.E., Rabinowitz M.H., and Renhowe P.A. Enantioselective total synthesis of (-)-ptilomycalin A. J Am Chem Soc 117 (1995) 2657-2658
    • (1995) J Am Chem Soc , vol.117 , pp. 2657-2658
    • Overman, L.E.1    Rabinowitz, M.H.2    Renhowe, P.A.3
  • 33
    • 1342302935 scopus 로고    scopus 로고
    • The tethered Biginelli condensation in natural product synthesis
    • Aron Z.D., and Overman L.E. The tethered Biginelli condensation in natural product synthesis. Chem Commun (2004) 253-265
    • (2004) Chem Commun , pp. 253-265
    • Aron, Z.D.1    Overman, L.E.2
  • 34
    • 0033615357 scopus 로고    scopus 로고
    • Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen
    • Mayer T.U., Kapoor T.M., Haggarty S.J., King R.W., Schreiber S.L., and Mitchison T.J. Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science 286 (1999) 971-974
    • (1999) Science , vol.286 , pp. 971-974
    • Mayer, T.U.1    Kapoor, T.M.2    Haggarty, S.J.3    King, R.W.4    Schreiber, S.L.5    Mitchison, T.J.6
  • 35
    • 0034674776 scopus 로고    scopus 로고
    • Lanthanide triflate catalyzed Biginelli reaction. One-pot synthesis of dihydropyrimidinones under solvent-free conditions
    • Ma Y., Qian C., Wang L., and Yang M. Lanthanide triflate catalyzed Biginelli reaction. One-pot synthesis of dihydropyrimidinones under solvent-free conditions. J Org Chem 65 (2000) 3864-3868
    • (2000) J Org Chem , vol.65 , pp. 3864-3868
    • Ma, Y.1    Qian, C.2    Wang, L.3    Yang, M.4
  • 36
    • 28444438118 scopus 로고    scopus 로고
    • Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: asymmetric synthesis of dihydropyrimidines
    • Huang Y., Yang F., and Zhu C. Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: asymmetric synthesis of dihydropyrimidines. J Am Chem Soc 127 (2005) 16386-16387
    • (2005) J Am Chem Soc , vol.127 , pp. 16386-16387
    • Huang, Y.1    Yang, F.2    Zhu, C.3
  • 37
    • 58849138719 scopus 로고    scopus 로고
    • A chemical placebo. NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis
    • This article catalogs more than 200 different conditions for the Biginelli reaction and cautions against over-interpretation of catalysis results.
    • Kolosov M.A., Orlov V.D., Beloborodov D.A., and Dotsenko V.V. A chemical placebo. NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis. Mol Divers 13 (2009) 5-25. This article catalogs more than 200 different conditions for the Biginelli reaction and cautions against over-interpretation of catalysis results.
    • (2009) Mol Divers , vol.13 , pp. 5-25
    • Kolosov, M.A.1    Orlov, V.D.2    Beloborodov, D.A.3    Dotsenko, V.V.4
  • 38
    • 70350307205 scopus 로고    scopus 로고
    • Highly enantioselective organocatalytic Biginelli and Biginelli-like condensations: reversal of the stereochemistry by tuning the 3,3′-disubstituents of phosphoric acids
    • Li N., Chen X.-H., Song J., Luo S.-W., Fan W., and Gong L.-Z. Highly enantioselective organocatalytic Biginelli and Biginelli-like condensations: reversal of the stereochemistry by tuning the 3,3′-disubstituents of phosphoric acids. J Am Chem Soc 131 (2009) 15301-15310
    • (2009) J Am Chem Soc , vol.131 , pp. 15301-15310
    • Li, N.1    Chen, X.-H.2    Song, J.3    Luo, S.-W.4    Fan, W.5    Gong, L.-Z.6
  • 39
    • 33845205051 scopus 로고    scopus 로고
    • Highly enantioselective organocatalytic Biginelli reaction
    • Chen X.-H., Xu X.-Y., Liu H., Cun L.-F., and Gong L.-Z. Highly enantioselective organocatalytic Biginelli reaction. J Am Chem Soc 128 (2006) 14802-14803
    • (2006) J Am Chem Soc , vol.128 , pp. 14802-14803
    • Chen, X.-H.1    Xu, X.-Y.2    Liu, H.3    Cun, L.-F.4    Gong, L.-Z.5
  • 40
    • 53849096413 scopus 로고    scopus 로고
    • An enantioselective Biginelli reaction catalyzed by a simple chiral secondary amine and achiral Bronsted acid by a dual-activation route
    • Xin J., Chang L., Hou Z., Shang D., Liu X., and Feng X. An enantioselective Biginelli reaction catalyzed by a simple chiral secondary amine and achiral Bronsted acid by a dual-activation route. Chem Eur J 14 (2008) 3177-3181
    • (2008) Chem Eur J , vol.14 , pp. 3177-3181
    • Xin, J.1    Chang, L.2    Hou, Z.3    Shang, D.4    Liu, X.5    Feng, X.6
  • 41
    • 73349112857 scopus 로고    scopus 로고
    • Highly enantioselective Biginelli reaction promoted by chiral bifunctional primary amine-thiourea catalysts: asymmetric synthesis of dihydropyrimidines
    • Wang Y., Yang H., Yu J., Miao Z., and Chen R. Highly enantioselective Biginelli reaction promoted by chiral bifunctional primary amine-thiourea catalysts: asymmetric synthesis of dihydropyrimidines. Adv Synth Catal 351 (2009) 3057-3062
    • (2009) Adv Synth Catal , vol.351 , pp. 3057-3062
    • Wang, Y.1    Yang, H.2    Yu, J.3    Miao, Z.4    Chen, R.5
  • 42
    • 23844490047 scopus 로고    scopus 로고
    • Asymmetric Mannich reactions of β-keto esters with acyl imines catalyzed by cinchona alkaloids
    • Lou S., Taoka B.M., Ting A., and Schaus S.E. Asymmetric Mannich reactions of β-keto esters with acyl imines catalyzed by cinchona alkaloids. J Am Chem Soc 127 (2005) 11256-11257
    • (2005) J Am Chem Soc , vol.127 , pp. 11256-11257
    • Lou, S.1    Taoka, B.M.2    Ting, A.3    Schaus, S.E.4
  • 44
    • 61349144309 scopus 로고    scopus 로고
    • An Ugi reaction in the total synthesis of (-)-dysibetaine
    • Isaacson J., and Kobayashi Y. An Ugi reaction in the total synthesis of (-)-dysibetaine. Angew Chem Int Ed 48 (2009) 1845-1848
    • (2009) Angew Chem Int Ed , vol.48 , pp. 1845-1848
    • Isaacson, J.1    Kobayashi, Y.2
  • 45
    • 33748512599 scopus 로고    scopus 로고
    • Versatile, fragrant, convertible isonitriles
    • Pirrung M.C., and Ghorai S. Versatile, fragrant, convertible isonitriles. J Am Chem Soc 128 (2006) 11772-11773
    • (2006) J Am Chem Soc , vol.128 , pp. 11772-11773
    • Pirrung, M.C.1    Ghorai, S.2
  • 46
    • 66249125675 scopus 로고    scopus 로고
    • Multicomponent reactions of convertible isonitriles
    • Pirrung includes interesting references and quotes relating to the stench associated with isonitriles.
    • Pirrung M.C., Ghorai S., and Ibarra-Rivera T.R. Multicomponent reactions of convertible isonitriles. J Org Chem 74 (2009) 4110-4117. Pirrung includes interesting references and quotes relating to the stench associated with isonitriles.
    • (2009) J Org Chem , vol.74 , pp. 4110-4117
    • Pirrung, M.C.1    Ghorai, S.2    Ibarra-Rivera, T.R.3
  • 47
    • 37749025206 scopus 로고    scopus 로고
    • A stable, convertible isonitrile as a formic acid carbanion [-COOH] equivalent and its application in multicomponent reactions
    • This article includes a summary of various 'convertible' isonitriles.
    • Kreye O., Westermann B., and Wessjohann L.A. A stable, convertible isonitrile as a formic acid carbanion [-COOH] equivalent and its application in multicomponent reactions. Synlett (2007) 3188-3192. This article includes a summary of various 'convertible' isonitriles.
    • (2007) Synlett , pp. 3188-3192
    • Kreye, O.1    Westermann, B.2    Wessjohann, L.A.3
  • 49
    • 9444230492 scopus 로고    scopus 로고
    • Stereochemical control of the Passerini reaction
    • Andreana P.R., Liu C.C., and Schreiber S.L. Stereochemical control of the Passerini reaction. Org Lett 6 (2004) 4231-4233
    • (2004) Org Lett , vol.6 , pp. 4231-4233
    • Andreana, P.R.1    Liu, C.C.2    Schreiber, S.L.3
  • 50
    • 54749125509 scopus 로고    scopus 로고
    • Catalytic enantioselective passerini three-component reaction
    • Wang S.-X., Wang M.-X., Wang D.-X., and Zhu J. Catalytic enantioselective passerini three-component reaction. Angew Chem Int Ed 120 (2008) 394-397
    • (2008) Angew Chem Int Ed , vol.120 , pp. 394-397
    • Wang, S.-X.1    Wang, M.-X.2    Wang, D.-X.3    Zhu, J.4
  • 51
    • 4644278676 scopus 로고    scopus 로고
    • Titanium catalysis in the Ugi reaction of α-amino acids with aromatic aldehydes
    • Godet T., Bonvin Y., Vincent G., Merle D., Thozet A., and Ciufolini M.A. Titanium catalysis in the Ugi reaction of α-amino acids with aromatic aldehydes. Org Lett 6 (2004) 3281-3284
    • (2004) Org Lett , vol.6 , pp. 3281-3284
    • Godet, T.1    Bonvin, Y.2    Vincent, G.3    Merle, D.4    Thozet, A.5    Ciufolini, M.A.6
  • 52
    • 0038369790 scopus 로고    scopus 로고
    • Microwave-assisted multi-component synthesis of fused 3-aminoimidazoles
    • Ireland S.M., Tye H., and Whittaker M. Microwave-assisted multi-component synthesis of fused 3-aminoimidazoles. Tetrahedron Lett 44 (2003) 4369-4371
    • (2003) Tetrahedron Lett , vol.44 , pp. 4369-4371
    • Ireland, S.M.1    Tye, H.2    Whittaker, M.3
  • 53
    • 0348048827 scopus 로고    scopus 로고
    • Novel α-amino amidine synthesis via scandium(III) triflate mediated 3CC Ugi condensation reaction
    • Keung W., Bakir F., Patron A.P., Rogers D., Priest C.D., and Darmohusodo V. Novel α-amino amidine synthesis via scandium(III) triflate mediated 3CC Ugi condensation reaction. Tetrahedron Lett 45 (2004) 733-737
    • (2004) Tetrahedron Lett , vol.45 , pp. 733-737
    • Keung, W.1    Bakir, F.2    Patron, A.P.3    Rogers, D.4    Priest, C.D.5    Darmohusodo, V.6
  • 54
    • 48249113283 scopus 로고    scopus 로고
    • Catalysis of Ugi four component coupling reactions by rare earth metal triflates
    • Okandeji B.O., Gordon J.R., and Sello J.K. Catalysis of Ugi four component coupling reactions by rare earth metal triflates. J Org Chem 73 (2008) 5595-5597
    • (2008) J Org Chem , vol.73 , pp. 5595-5597
    • Okandeji, B.O.1    Gordon, J.R.2    Sello, J.K.3
  • 55
    • 50849087128 scopus 로고    scopus 로고
    • Catalytic three-component Ugi reaction
    • Pan S.C., and List B. Catalytic three-component Ugi reaction. Angew Chem Int Ed 47 (2008) 3622-3625
    • (2008) Angew Chem Int Ed , vol.47 , pp. 3622-3625
    • Pan, S.C.1    List, B.2
  • 56
    • 0031055591 scopus 로고    scopus 로고
    • A new and practical synthesis of a-amino acids from alkenyl boronic acids
    • Petasis N.A., and Zavialov I.A. A new and practical synthesis of a-amino acids from alkenyl boronic acids. J Am Chem Soc 119 (1997) 445-446
    • (1997) J Am Chem Soc , vol.119 , pp. 445-446
    • Petasis, N.A.1    Zavialov, I.A.2
  • 57
    • 0037136116 scopus 로고    scopus 로고
    • The first example of chiral induction using homochiral boronic esters in the Petasis reaction
    • Koolmeister T., Ŝdergren M., and Scobie M. The first example of chiral induction using homochiral boronic esters in the Petasis reaction. Tetrahedron Lett 43 (2002) 5969-5970
    • (2002) Tetrahedron Lett , vol.43 , pp. 5969-5970
    • Koolmeister, T.1    Ŝdergren, M.2    Scobie, M.3
  • 58
    • 0032544945 scopus 로고    scopus 로고
    • Highly stereocontrolled one-step synthesis of anti-β-amino alcohols from organoboronic acids, amines, and α-hydroxy aldehydes
    • Petasis N.A., and Zavialov I.A. Highly stereocontrolled one-step synthesis of anti-β-amino alcohols from organoboronic acids, amines, and α-hydroxy aldehydes. J Am Chem Soc 120 (1998) 11798-11799
    • (1998) J Am Chem Soc , vol.120 , pp. 11798-11799
    • Petasis, N.A.1    Zavialov, I.A.2
  • 59
    • 2942616521 scopus 로고    scopus 로고
    • α-Aminoallylation of aldehydes with ammonia: stereoselective synthesis of homoallylic primary amines
    • Sugiura M., Hirano K., and Kobayashi S. α-Aminoallylation of aldehydes with ammonia: stereoselective synthesis of homoallylic primary amines. J Am Chem Soc 126 (2004) 7182-7183
    • (2004) J Am Chem Soc , vol.126 , pp. 7182-7183
    • Sugiura, M.1    Hirano, K.2    Kobayashi, S.3
  • 60
    • 63349103575 scopus 로고    scopus 로고
    • A mild, one-pot synthesis of arylamines via palladium-catalyzed addition of aryl aldehydes with amines and arylboronic acids in water
    • Yu A., Wu Y., Cheng B., Wei K., and Li J. A mild, one-pot synthesis of arylamines via palladium-catalyzed addition of aryl aldehydes with amines and arylboronic acids in water. Adv Synth Catal 351 (2009) 767-771
    • (2009) Adv Synth Catal , vol.351 , pp. 767-771
    • Yu, A.1    Wu, Y.2    Cheng, B.3    Wei, K.4    Li, J.5
  • 62
    • 51649092172 scopus 로고    scopus 로고
    • Synthesis of (+)-uniflorine a: a structural reassignment and a configurational assignment
    • Ritthiwigrom T., and Pyne S.G. Synthesis of (+)-uniflorine a: a structural reassignment and a configurational assignment. Org Lett 10 (2008) 2769-2771
    • (2008) Org Lett , vol.10 , pp. 2769-2771
    • Ritthiwigrom, T.1    Pyne, S.G.2
  • 63
    • 34249793225 scopus 로고    scopus 로고
    • Catalytic enantioselective Petasis-type reaction of quinolines catalyzed by a newly designed thiourea catalyst
    • Yamaoka Y., Miyabe H., and Takemoto Y. Catalytic enantioselective Petasis-type reaction of quinolines catalyzed by a newly designed thiourea catalyst. J Am Chem Soc 129 (2007) 6686-6687
    • (2007) J Am Chem Soc , vol.129 , pp. 6686-6687
    • Yamaoka, Y.1    Miyabe, H.2    Takemoto, Y.3
  • 64
    • 44449092080 scopus 로고    scopus 로고
    • Asymmetric Petasis reactions catalyzed by chiral biphenols
    • Lou S., and Schaus S.E. Asymmetric Petasis reactions catalyzed by chiral biphenols. J Am Chem Soc 130 (2008) 6922-6923
    • (2008) J Am Chem Soc , vol.130 , pp. 6922-6923
    • Lou, S.1    Schaus, S.E.2
  • 65
    • 35948929153 scopus 로고    scopus 로고
    • Petasis borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. An efficient one-pot route to stereodefined α-amino acids and homoallyl alcohols
    • Selander N., Kipke A., Sebelius S., and Szabo K.J. Petasis borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. An efficient one-pot route to stereodefined α-amino acids and homoallyl alcohols. J Am Chem Soc 129 (2007) 13723-13731
    • (2007) J Am Chem Soc , vol.129 , pp. 13723-13731
    • Selander, N.1    Kipke, A.2    Sebelius, S.3    Szabo, K.J.4
  • 66
    • 60849104808 scopus 로고    scopus 로고
    • Diversity-oriented synthesis and preliminary biological screening of highly substituted five-membered lactones and lactams originating from an allylboration of aldehydes and imines
    • Elford T.G., Ulaczyk-Lesanko A., De Pascale G., Wright G.D., and Hall D.G. Diversity-oriented synthesis and preliminary biological screening of highly substituted five-membered lactones and lactams originating from an allylboration of aldehydes and imines. J Comb Chem 11 (2009) 155-168
    • (2009) J Comb Chem , vol.11 , pp. 155-168
    • Elford, T.G.1    Ulaczyk-Lesanko, A.2    De Pascale, G.3    Wright, G.D.4    Hall, D.G.5
  • 67
    • 33750616720 scopus 로고    scopus 로고
    • An expedient route to diaza-spirocycles utilizing a sequential multicomponent α-aminoallylation/ring-closing metathesis strategy
    • Gracias V., Gasiecki A.F., Moore J.D., Akritopoulou-Zanze I., and Djuric S.W. An expedient route to diaza-spirocycles utilizing a sequential multicomponent α-aminoallylation/ring-closing metathesis strategy. Tetrahedron Lett 47 (2006) 8977-8980
    • (2006) Tetrahedron Lett , vol.47 , pp. 8977-8980
    • Gracias, V.1    Gasiecki, A.F.2    Moore, J.D.3    Akritopoulou-Zanze, I.4    Djuric, S.W.5
  • 68
    • 65349158254 scopus 로고    scopus 로고
    • Cyclic anhydrides in formal cycloadditions and multicomponent reactions
    • Gonzalez-Lopez M., and Shaw J.T. Cyclic anhydrides in formal cycloadditions and multicomponent reactions. Chem Rev 109 (2009) 164-189
    • (2009) Chem Rev , vol.109 , pp. 164-189
    • Gonzalez-Lopez, M.1    Shaw, J.T.2
  • 69
    • 0014591941 scopus 로고
    • The condensation of succinic anhydride with benzylidinemethylamine. A stereoselective synthesis of trans- and cis-1-methyl-4-carbosy-5-phenyl-2-pyrrolidinone
    • Castagnoli Jr. N. The condensation of succinic anhydride with benzylidinemethylamine. A stereoselective synthesis of trans- and cis-1-methyl-4-carbosy-5-phenyl-2-pyrrolidinone. J Org Chem 34 (1969) 3187-3189
    • (1969) J Org Chem , vol.34 , pp. 3187-3189
    • Castagnoli Jr., N.1
  • 70
    • 0017481695 scopus 로고
    • Condensation of imines with homophthalic anhydrides. A convergent synthesis of cis- and trans-13-methyltetrahydroprotoberberines
    • Cushman M., Gentry J., and Dekow F.W. Condensation of imines with homophthalic anhydrides. A convergent synthesis of cis- and trans-13-methyltetrahydroprotoberberines. J Org Chem 42 (1977) 1111-1116
    • (1977) J Org Chem , vol.42 , pp. 1111-1116
    • Cushman, M.1    Gentry, J.2    Dekow, F.W.3
  • 71
    • 0000319547 scopus 로고
    • A study and mechanistic interpretation of the electronic and steric effects that determine the stereochemical outcome of the reaction of Schiff bases with homophthalic anhydride and 3-phenylsuccinic anhydride
    • Cushman M., and Madaj E.J. A study and mechanistic interpretation of the electronic and steric effects that determine the stereochemical outcome of the reaction of Schiff bases with homophthalic anhydride and 3-phenylsuccinic anhydride. J Org Chem 52 (1987) 907-915
    • (1987) J Org Chem , vol.52 , pp. 907-915
    • Cushman, M.1    Madaj, E.J.2
  • 72
    • 0037416916 scopus 로고    scopus 로고
    • Room temperature ionic liquids promoted three-component coupling reactions: a facile synthesis of cis-isoquinolonic acids
    • Yadav J.S., Reddy B.V.S., Saritha R.K., and Prasad A.R. Room temperature ionic liquids promoted three-component coupling reactions: a facile synthesis of cis-isoquinolonic acids. Tetrahedron 59 (2003) 1805-1809
    • (2003) Tetrahedron , vol.59 , pp. 1805-1809
    • Yadav, J.S.1    Reddy, B.V.S.2    Saritha, R.K.3    Prasad, A.R.4
  • 73
    • 18244366861 scopus 로고    scopus 로고
    • One-pot synthesis of cis-isoquinolonic acid derivatives via three-component reaction of homophthalic anhydride with aldehydes and amines using ytterbium(III) triflate as catalyst
    • Wang L., Liu J., Tian H., Qian C., and Sun J. One-pot synthesis of cis-isoquinolonic acid derivatives via three-component reaction of homophthalic anhydride with aldehydes and amines using ytterbium(III) triflate as catalyst. Adv Synth Catal 347 (2005) 689-694
    • (2005) Adv Synth Catal , vol.347 , pp. 689-694
    • Wang, L.1    Liu, J.2    Tian, H.3    Qian, C.4    Sun, J.5
  • 74
    • 35048870516 scopus 로고    scopus 로고
    • Diastereoselective synthesis of gamma-lactams by a one-pot, four-component reaction
    • Wei J., and Shaw J.T. Diastereoselective synthesis of gamma-lactams by a one-pot, four-component reaction. Org Lett 9 (2007) 4077-4080
    • (2007) Org Lett , vol.9 , pp. 4077-4080
    • Wei, J.1    Shaw, J.T.2
  • 75
    • 36749025633 scopus 로고    scopus 로고
    • Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
    • Galliford C.V., and Scheidt K.A. Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents. Angew Chem Int Ed 46 (2007) 8748-8758
    • (2007) Angew Chem Int Ed , vol.46 , pp. 8748-8758
    • Galliford, C.V.1    Scheidt, K.A.2
  • 76
    • 0034647225 scopus 로고    scopus 로고
    • The asymmetric total synthesis of (+)- and (-)-spirotryprostatin B
    • Sebahar P.R., and Williams R.M. The asymmetric total synthesis of (+)- and (-)-spirotryprostatin B. J Am Chem Soc 122 (2000) 5666-5667
    • (2000) J Am Chem Soc , vol.122 , pp. 5666-5667
    • Sebahar, P.R.1    Williams, R.M.2
  • 77
    • 42649137921 scopus 로고    scopus 로고
    • Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: control of stereochemistry via a chiral Bronsted acid activated dipole
    • Chen X.-H., Zhang W.-Q., and Gong L.-Z. Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: control of stereochemistry via a chiral Bronsted acid activated dipole. J Am Chem Soc 130 (2008) 5652-5653
    • (2008) J Am Chem Soc , vol.130 , pp. 5652-5653
    • Chen, X.-H.1    Zhang, W.-Q.2    Gong, L.-Z.3
  • 78
    • 10344242467 scopus 로고    scopus 로고
    • A library of spirooxindoles based on a stereoselective three-component coupling reaction
    • Lo M.M.C., Neumann C.S., Nagayama S., Perlstein E.O., and Schreiber S.L. A library of spirooxindoles based on a stereoselective three-component coupling reaction. J Am Chem Soc 126 (2004) 16077-16086
    • (2004) J Am Chem Soc , vol.126 , pp. 16077-16086
    • Lo, M.M.C.1    Neumann, C.S.2    Nagayama, S.3    Perlstein, E.O.4    Schreiber, S.L.5
  • 79
    • 75749152357 scopus 로고    scopus 로고
    • Multicomponent reaction discovery: Three-component synthesis of spirooxindoles
    • Liang B, Kalidindi S, Porco JA, Jr., Stephenson CRJ: Multicomponent reaction discovery: three-component synthesis of spirooxindoles. Org Lett, 572-575.
    • Org Lett , pp. 572-575
    • Liang, B.1    Kalidindi, S.2    Porco Jr., J.A.3    Stephenson, C.R.J.4
  • 80
    • 71749102280 scopus 로고    scopus 로고
    • Grindstone chemistry: one-pot synthesis of spiro[diindenopyridine-indoline]triones and spiro[acenaphthylene-diindenopyridine]triones
    • Ghahremanzadeh R., Ahadi S., Shakibaei G.I., and Bazgir A. Grindstone chemistry: one-pot synthesis of spiro[diindenopyridine-indoline]triones and spiro[acenaphthylene-diindenopyridine]triones. Tetrahedron Lett 51 (2010) 499-502
    • (2010) Tetrahedron Lett , vol.51 , pp. 499-502
    • Ghahremanzadeh, R.1    Ahadi, S.2    Shakibaei, G.I.3    Bazgir, A.4
  • 81
    • 70349784950 scopus 로고    scopus 로고
    • Targeting structural and stereochemical complexity by organocascade catalysis: construction of spirocyclic oxindoles having multiple stereocenters
    • Giorgio B., Li-Yuan W., Andrea M., Berardino G., Fabio P., Mao-Ping S., Giuseppe B., and Paolo M. Targeting structural and stereochemical complexity by organocascade catalysis: construction of spirocyclic oxindoles having multiple stereocenters. Angew Chem Int Ed 48 (2009) 7200-7203
    • (2009) Angew Chem Int Ed , vol.48 , pp. 7200-7203
    • Giorgio, B.1    Li-Yuan, W.2    Andrea, M.3    Berardino, G.4    Fabio, P.5    Mao-Ping, S.6    Giuseppe, B.7    Paolo, M.8
  • 82
    • 67650466820 scopus 로고    scopus 로고
    • Asymmetric organocatalytic four-component quadruple domino reaction initiated by oxa-Michael addition of alcohols to acrolein
    • Zhang F.-L., Xu A.-W., Gong Y.-F., Wei M.-H., and Yang X.-L. Asymmetric organocatalytic four-component quadruple domino reaction initiated by oxa-Michael addition of alcohols to acrolein. Chem Eur J 15 (2009) 6815-6818
    • (2009) Chem Eur J , vol.15 , pp. 6815-6818
    • Zhang, F.-L.1    Xu, A.-W.2    Gong, Y.-F.3    Wei, M.-H.4    Yang, X.-L.5
  • 83
    • 70349906887 scopus 로고    scopus 로고
    • Nickel-catalyzed three-component [2 + 2 + 2] cycloaddition reaction of arynes, alkenes, and alkynes
    • Qiu Z., and Xie Z. Nickel-catalyzed three-component [2 + 2 + 2] cycloaddition reaction of arynes, alkenes, and alkynes. Angew Chem Int Ed 48 (2009) 5729-5732
    • (2009) Angew Chem Int Ed , vol.48 , pp. 5729-5732
    • Qiu, Z.1    Xie, Z.2
  • 84
    • 34250826643 scopus 로고    scopus 로고
    • Palladium-catalyzed, sequential, three-component cross-coupling of aryl halides, alkynes, and arynes
    • Liu Z., and Larock R.C. Palladium-catalyzed, sequential, three-component cross-coupling of aryl halides, alkynes, and arynes. Angew Chem Int Ed 46 (2007) 2535-2538
    • (2007) Angew Chem Int Ed , vol.46 , pp. 2535-2538
    • Liu, Z.1    Larock, R.C.2
  • 85
    • 65249190929 scopus 로고    scopus 로고
    • Concise synthesis of tricyclic isoindolinones via one-pot cascade multicomponent sequences
    • Medimagh R., Marque S., Prim D., Marrot J., and Chatti S. Concise synthesis of tricyclic isoindolinones via one-pot cascade multicomponent sequences. Org Lett 11 (2009) 1817-1820
    • (2009) Org Lett , vol.11 , pp. 1817-1820
    • Medimagh, R.1    Marque, S.2    Prim, D.3    Marrot, J.4    Chatti, S.5
  • 86
    • 29044446242 scopus 로고    scopus 로고
    • Multicomponent domino reaction from β-ketoamides: highly efficient access to original polyfunctionalized 2,6-diazabicyclo[2.2.2]octane cores
    • Lieby-Muller F., Constantieux T., and Rodriguez J. Multicomponent domino reaction from β-ketoamides: highly efficient access to original polyfunctionalized 2,6-diazabicyclo[2.2.2]octane cores. J Am Chem Soc 127 (2005) 17176-17177
    • (2005) J Am Chem Soc , vol.127 , pp. 17176-17177
    • Lieby-Muller, F.1    Constantieux, T.2    Rodriguez, J.3
  • 87
    • 69049086649 scopus 로고    scopus 로고
    • Four-component domino reaction leading to multifunctionalized quinazolines
    • Jiang B., Tu S.-J., Kaur P., Wever W., and Li G. Four-component domino reaction leading to multifunctionalized quinazolines. J Am Chem Soc 131 (2009) 11660-11661
    • (2009) J Am Chem Soc , vol.131 , pp. 11660-11661
    • Jiang, B.1    Tu, S.-J.2    Kaur, P.3    Wever, W.4    Li, G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.