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Volumn 15, Issue 13, 2011, Pages 2083-2097

Umpolung catalysis in benzoin-type and stetter-type reactions: From enzymatic performances to bio-mimetic organocatalytic concepts

Author keywords

Acyloin; Benzoin; Biocatalysis; Biomimetic; Organocatalysis; Stetter

Indexed keywords

BIOMIMETICS; CATALYSIS; ENZYMES; HYDROPHOBICITY;

EID: 79959325739     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211796150679     Document Type: Article
Times cited : (26)

References (88)
  • 2
    • 0032736221 scopus 로고    scopus 로고
    • Biocatalytic synthesis of optically active α-oxyfunctionalized carbonyl compounds
    • Adam, W.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Biocatalytic synthesis of optically active α-oxyfunctionalized carbonyl compounds. Acc. Chem. Res., 1999, 32, 837-845.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 837-845
    • Adam, W.1    Lazarus, M.2    Saha-Möller, C.R.3    Schreier, P.4
  • 3
    • 0000043848 scopus 로고
    • Asymmetric hydroxylation of enolates with Nsulfonyloxaziridines
    • Davis, F. A.; Chen, B. C. Asymmetric hydroxylation of enolates with Nsulfonyloxaziridines. Chem. Rev., 1992, 92, 919-934.
    • (1992) Chem. Rev. , vol.92 , pp. 919-934
    • Davis, F.A.1    Chen, B.C.2
  • 4
    • 0037391206 scopus 로고    scopus 로고
    • Current mechanistic understanding of thiamin diphosphatedependent enzymatic reactions
    • Jordan, F. Current mechanistic understanding of thiamin diphosphatedependent enzymatic reactions. Nat. Prod. Rep. 2003, 20, 184-201.
    • (2003) Nat. Prod. Rep. , vol.20 , pp. 184-201
    • Jordan, F.1
  • 5
    • 65549162613 scopus 로고    scopus 로고
    • Thiamine diphosphate in biological chemistry: Exploitation of diverse thiamine diphospahte dependent enzymes for asymmetric chemoenzymatic synthesis
    • Müller, M.; Gocke, D.; Pohl, M. Thiamine diphosphate in biological chemistry: exploitation of diverse thiamine diphospahte dependent enzymes for asymmetric chemoenzymatic synthesis. FEBS J., 2009, 276, 2894-2904.
    • (2009) FEBS J , vol.276 , pp. 2894-2904
    • Müller, M.1    Gocke, D.2    Pohl, M.3
  • 6
    • 36448983239 scopus 로고    scopus 로고
    • Thiamine pyrophosphate dependent enzyme catalyzed reactions: Stereoselective C-C bond formations in water
    • Demir, A. S.; Ayhan, P.; Betül Sopaci, S. Thiamine pyrophosphate dependent enzyme catalyzed reactions: Stereoselective C-C bond formations in water. Clean: Soil, Air, Water, 2007, 35, 406-412.
    • (2007) Clean: Soil, Air, Water , vol.35 , pp. 406-412
    • Demir, A.S.1    Ayhan, P.2    Betül sopaci, S.3
  • 8
    • 0042628455 scopus 로고    scopus 로고
    • Thiamine-diphosphate dependent enzymes: New aspects of asymmetric C-C bond formation
    • Pohl, M.; Lingen, B.; Müller, M. Thiamine-diphosphate dependent enzymes: new aspects of asymmetric C-C bond formation. Chem. Eur. J., 2002, 8, 5288-5295.
    • (2002) Chem. Eur. J. , vol.8 , pp. 5288-5295
    • Pohl, M.1    Lingen, B.2    Müller, M.3
  • 9
    • 76549107425 scopus 로고    scopus 로고
    • Entwicklung einer Enzymplattform für die biokatalytische C-C Verknüpfung
    • Gocke, D.; Kolter, G.; Müller, M.; Pohl, M. Entwicklung einer Enzymplattform für die biokatalytische C-C Verknüpfung. Chem. Ing. Tech., 2010, 82, 81-86.
    • (2010) Chem. Ing. Tech. , vol.82 , pp. 81-86
    • Gocke, D.1    Kolter, G.2    Müller, M.3    Pohl, M.4
  • 11
    • 2242484782 scopus 로고
    • Zur Kenntnis der Carboligase; IV Mitteilung: Weitere Feststellungen über die biosynthetische Kohlenstoffkettenverknüpfung beim Gärungsvorgange
    • Neuberg, C.; Ohle, H. Zur Kenntnis der Carboligase; IV Mitteilung: Weitere Feststellungen über die biosynthetische Kohlenstoffkettenverknüpfung beim Gärungsvorgange. Biochem. Z., 1992, 128, 610-618.
    • (1992) Biochem. Z. , vol.128 , pp. 610-618
    • Neuberg, C.1    Ohle, H.2
  • 12
    • 0000921648 scopus 로고
    • Über ein Kohlenstoffketten knüpfendes Ferment (Carboligase)
    • Neuberg, C., Hirsch, J. Über ein Kohlenstoffketten knüpfendes Ferment (Carboligase). Biochem. Z., 1921, 115, 282-310.
    • (1921) Biochem. Z. , vol.115 , pp. 282-310
    • Neuberg, C.1    Hirsch, J.2
  • 15
    • 77952956848 scopus 로고    scopus 로고
    • Enantioselective intermolecular aldehyde-ketone cross-coupling through an enzymatic carboligation reaction
    • Lehwald, P.; Richter, M.; Röhr, C.; Liu, H. W.; Müller, M. Enantioselective intermolecular aldehyde-ketone cross-coupling through an enzymatic carboligation reaction. Angew. Chem. Int. Ed., 2010, 49, 2389-2392.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2389-2392
    • Lehwald, P.1    Richter, M.2    Röhr, C.3    Liu, H.W.4    Müller, M.5
  • 16
    • 10044248344 scopus 로고    scopus 로고
    • Catalytic promiscuity in biocatalysis: Using old enzymes to form new bonds and follow new pathways
    • Bornscheuer, U. T.; Kazlauskas, R. J. Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways. Angew. Chem. Int. Ed., 2004, 43, 6032-6040.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 6032-6040
    • Bornscheuer, U.T.1    Kazlauskas, R.J.2
  • 18
    • 34247131307 scopus 로고    scopus 로고
    • Enzyme promiscuity: Mechanism and applications
    • Hult, K.; Berglund, P. Enzyme promiscuity: mechanism and applications. Trends. Biotechnol., 2007, 25, 231-238.
    • (2007) Trends Biotechnol , vol.25 , pp. 231-238
    • Hult, K.1    Berglund, P.2
  • 20
    • 0035793248 scopus 로고    scopus 로고
    • The application of L-Proline as an enzyme mimic and further new asymmetric syntheses using small organic molecules as chiral catalysts
    • Gröger, H.; Wilken, J. The application of L-Proline as an enzyme mimic and further new asymmetric syntheses using small organic molecules as chiral catalysts. Angew. Chem. Int. Ed., 2001, 40, 529-532.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 529-532
    • Gröger, H.1    Wilken, J.2
  • 21
    • 79957779161 scopus 로고    scopus 로고
    • Minimal Hydrolases: Organocatalytic ring-opening polymerizations catalyzed by naturally-occurring carboxylic acids
    • Domínguez de María, P. Minimal Hydrolases: Organocatalytic ring-opening polymerizations catalyzed by naturally-occurring carboxylic acids. Chem- CatChem, 2010, 2, 487-492.
    • (2010) Chem- CatChem , vol.2 , pp. 487-492
    • Domínguez de María, P.1
  • 22
    • 53849130681 scopus 로고    scopus 로고
    • Lessons from Nature: Biomimetic Organocatalytic Carbon-Carbon Bond Formations
    • Enders, D.; Narine, A. A. Lessons from Nature: Biomimetic Organocatalytic Carbon-Carbon Bond Formations. J. Org. Chem., 2008, 73, 7857-7870.
    • (2008) J. Org. Chem. , vol.73 , pp. 7857-7870
    • Enders, D.1    Narine, A.A.2
  • 23
    • 64249157804 scopus 로고    scopus 로고
    • Biomimetic Organocatalytic C-CBond Formations
    • M. T. Reetz, B. List, S. Jaroch, H. Weinmann (Eds.), Springer-Verlag, Berlin
    • Enders, D.; Hüttl, M. R. M.; Niemeier, O. Biomimetic Organocatalytic C-CBond Formations. In Organocatalysis, M. T. Reetz, B. List, S. Jaroch, H. Weinmann (Eds.), Springer-Verlag, Berlin, 2008, 45-124.
    • (2008) Organocatalysis , pp. 45-124
    • Enders, D.1    Hüttl, M.R.M.2    Niemeier, O.3
  • 24
    • 77949568536 scopus 로고    scopus 로고
    • Microemulsion-based organogels as matrices for lipase immobilization
    • Zoumpanioti, M.; Stamatis, H.; Xenakis, A. Microemulsion-based organogels as matrices for lipase immobilization. Biotech. Adv. 2010, 28, 395-406.
    • (2010) Biotech. Adv. , vol.28 , pp. 395-406
    • Zoumpanioti, M.1    Stamatis, H.2    Xenakis, A.3
  • 26
    • 37049127435 scopus 로고
    • Acyloin condensation of aldehydes catalyzed by NLaurylthiazolium bromide
    • Tagaki, W.; Hara, H. Acyloin condensation of aldehydes catalyzed by NLaurylthiazolium bromide. J. Chem. Soc. Chem. Comm., 1973, 891.
    • (1973) J. Chem. Soc. Chem. Comm. , pp. 891
    • Tagaki, W.1    Hara, H.2
  • 27
    • 33845728625 scopus 로고    scopus 로고
    • Enamine-based aldol organocatalysis in water: Are they really "all wet
    • Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Enamine-based aldol organocatalysis in water: Are they really "all wet". Angew. Chem. Int. Ed., 2006, 45, 8100-8102.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 8100-8102
    • Brogan, A.P.1    Dickerson, T.J.2    Janda, K.D.3
  • 28
    • 33845788846 scopus 로고    scopus 로고
    • In water or in the presence of water?
    • Hayashi, Y. In water or in the presence of water?. Angew. Chem. Int. Ed., 2006, 45, 8103-8104.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 8103-8104
    • Hayashi, Y.1
  • 29
    • 0000121695 scopus 로고
    • Asymmetric bezoin condensation catalyzed by optically active thiazolium salts in micellar two-phase media
    • Tagaki, W.; Tamura, Y.; Yano, Y. Asymmetric bezoin condensation catalyzed by optically active thiazolium salts in micellar two-phase media. Bull. Chem. Soc. Jpn., 1980, 53, 478-480.
    • (1980) Bull. Chem. Soc. Jpn. , vol.53 , pp. 478-480
    • Tagaki, W.1    Tamura, Y.2    Yano, Y.3
  • 30
    • 85047673665 scopus 로고
    • A holoenzyme model of thiamin dependent enzyme; Asymmetrical acyloin condensation using a lipid catalyst in a bilayer membrane
    • Yamashita, K.; Sasaki, S.; Osaki, T.; Nango, M.; Tsuda, K. A holoenzyme model of thiamin dependent enzyme; Asymmetrical acyloin condensation using a lipid catalyst in a bilayer membrane. Tetrahedron Lett., 1995, 36, 4817-4820.
    • (1995) Tetrahedron Lett , vol.36 , pp. 4817-4820
    • Yamashita, K.1    Sasaki, S.2    Osaki, T.3    Nango, M.4    Tsuda, K.5
  • 31
    • 17444420408 scopus 로고
    • Oxidation of aldehydes by thiazolium ions and flavin in a cationic micelle
    • Yano, Y.; Hoshino, Y.; Tagaki, W. Oxidation of aldehydes by thiazolium ions and flavin in a cationic micelle. Chem. Lett., 1980, 749-752.
    • (1980) Chem. Lett. , pp. 749-752
    • Yano, Y.1    Hoshino, Y.2    Tagaki, W.3
  • 32
    • 0030814465 scopus 로고    scopus 로고
    • Multistep synthesis on the surface of selfassembled thiolate monolayers on gold: Probing the mechanism of the thiazolium-promoted acyloin condensation
    • Motesharei, K.; Myles, D. C. Multistep synthesis on the surface of selfassembled thiolate monolayers on gold: Probing the mechanism of the thiazolium-promoted acyloin condensation. J. Am. Chem. Soc., 1997, 119, 6674-6675.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 6674-6675
    • Motesharei, K.1    Myles, D.C.2
  • 33
    • 33845183143 scopus 로고
    • Catalytic Cyclophanes. 4. Supramolecular catalysis of benzoin condensations by a thiazolium cyclophane
    • Diederich, F.; Lutter, H. D. Catalytic Cyclophanes. 4. Supramolecular catalysis of benzoin condensations by a thiazolium cyclophane. J. Am. Chem. Soc., 1989, 111, 8438-8446.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8438-8446
    • Diederich, F.1    Lutter, H.D.2
  • 34
    • 84985580891 scopus 로고
    • Synthesis of a macrocyclic thiazolium-host and supramolecular catalysis of the benzoin condensation
    • Lutter, H. D.; Diederich, F. Synthesis of a macrocyclic thiazolium-host and supramolecular catalysis of the benzoin condensation. Angew. Chem. Int. Ed., 1986, 25, 1125-1127.
    • (1986) Angew. Chem. Int. Ed. , vol.25 , pp. 1125-1127
    • Lutter, H.D.1    Diederich, F.2
  • 35
    • 37049079815 scopus 로고
    • Enhancement of the rate of oxidative decarboxylation of pyruvic acid catalyzed by crowned thiazolium in the presence of alkali metal cations in ethanol
    • Yano, Y.; Kimura, M.; Shimaoka, K.; Iwasaki, H. Enhancement of the rate of oxidative decarboxylation of pyruvic acid catalyzed by crowned thiazolium in the presence of alkali metal cations in ethanol. J. Chem. Soc. Chem. Comm., 1986, 160-161.
    • (1986) J. Chem. Soc. Chem. Comm. , pp. 160-161
    • Yano, Y.1    Kimura, M.2    Shimaoka, K.3    Iwasaki, H.4
  • 36
    • 0000831276 scopus 로고
    • γ-cyclodextrin thiazolium salt holoenzyme mimic for the benzoin condensation
    • Breslow, R.; Kool, E. γ-cyclodextrin thiazolium salt holoenzyme mimic for the benzoin condensation. Tetrahedron Lett., 1988, 29, 1635-1638.
    • (1988) Tetrahedron Lett , vol.29 , pp. 1635-1638
    • Breslow, R.1    Kool, E.2
  • 37
    • 0000729815 scopus 로고
    • Functionalized cyclodextrins as holoenzyme mimics of thiamine-dependent enzymes
    • Hilvert, D.; Breslow, R. Functionalized cyclodextrins as holoenzyme mimics of thiamine-dependent enzymes. Bioorg. Chem., 1984, 12, 206-220.
    • (1984) Bioorg. Chem. , vol.12 , pp. 206-220
    • Hilvert, D.1    Breslow, R.2
  • 39
    • 0344255816 scopus 로고    scopus 로고
    • Lewis Acids: From conventional homogeneous to green homogeneous and heterogeneous catalysis
    • Corma, A.; García, H. Lewis Acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis. Chem. Rev., 2003, 103, 11, 4307-4365.
    • (2003) Chem. Rev. , vol.103 , Issue.11 , pp. 4307-4365
    • Corma, A.1    García, H.2
  • 40
    • 34548321007 scopus 로고    scopus 로고
    • Thiazolium salt immobilized on ionic liquid: An efficient catalyst and solvent for preparation of α-hydroxy-ketones
    • Mohanazadeh, F.; Aghvami, M. Thiazolium salt immobilized on ionic liquid: An efficient catalyst and solvent for preparation of α-hydroxy-ketones. Phosporous, Sulfur, and Silicon and the related elements, 2007, 182, 2467-2475.
    • (2007) Phosporous, Sulfur, and Silicon and The Related Elements , vol.182 , pp. 2467-2475
    • Mohanazadeh, F.1    Aghvami, M.2
  • 41
    • 54749118066 scopus 로고    scopus 로고
    • Non-solvents applications of ionic liquids in biotransformations and organocatalysis
    • Domínguez de María, P. Non-solvents applications of ionic liquids in biotransformations and organocatalysis. Angew. Chem. Int. Ed., 2008, 47, 6960-6968.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6960-6968
    • Domínguez de María, P.1
  • 42
    • 0036591570 scopus 로고    scopus 로고
    • The formose reaction on a synthetic zeolite impregnated with thiazolium catalyst
    • Tajima, H.; Tabata, K.; Nütsu, T.; Inoue, H. The formose reaction on a synthetic zeolite impregnated with thiazolium catalyst. J. Chem. Eng. Jpn., 2002, 35, 564-568.
    • (2002) J. Chem. Eng. Jpn. , vol.35 , pp. 564-568
    • Tajima, H.1    Tabata, K.2    Nütsu, T.3    Inoue, H.4
  • 43
    • 0033663132 scopus 로고    scopus 로고
    • Repeated use of thiazolium catalyst immobilized on cation-exchange resin
    • Tajima, H.; Nütsu, T.; Inoue, H. Repeated use of thiazolium catalyst immobilized on cation-exchange resin. J. Chem. Eng. Jpn., 2000, 33, 793-796.
    • (2000) J. Chem. Eng. Jpn. , vol.33 , pp. 793-796
    • Tajima, H.1    Nütsu, T.2    Inoue, H.3
  • 44
    • 21844470712 scopus 로고
    • Quaternization and catalytic activity of poly(vinylthiazoles)
    • Schilling, C. L.; Mulvaney, J. E. Quaternization and catalytic activity of poly(vinylthiazoles). Macromolecules, 1968, 1, 452-455.
    • (1968) Macromolecules , vol.1 , pp. 452-455
    • Schilling, C.L.1    Mulvaney, J.E.2
  • 45
    • 33748261370 scopus 로고
    • A. Polymer-supported thiazolium salt catalysts: A model system for the thiamine dependent enzymes
    • Sell, C. S.; Dorman, L. A. Polymer-supported thiazolium salt catalysts: A model system for the thiamine dependent enzymes. J. Chem. Soc. Chem. Comm., 1982, 629-630.
    • (1982) J. Chem. Soc. Chem. Comm. , pp. 629-630
    • Sell, C.S.1    Dorman, L.2
  • 46
    • 84986440328 scopus 로고
    • Application of polymer-bound thiazolium salts to the synthesis of acyloins and benzoins: Effects of solvent and substituents of the thiazolium nucleus
    • Karimian, K.; Mohanazadeh, F.; Rezai, S. Application of polymer-bound thiazolium salts to the synthesis of acyloins and benzoins: Effects of solvent and substituents of the thiazolium nucleus. J. Heterocyclic Chem., 1983, 20, 1119-1121.
    • (1983) J. Heterocyclic Chem. , vol.20 , pp. 1119-1121
    • Karimian, K.1    Mohanazadeh, F.2    Rezai, S.3
  • 47
    • 0024639572 scopus 로고
    • Polymer-bound thiamine models part II. Polymer effects on the catalytic activity of a macroreticular polystyrene-bound thiazolium salt in the benzoin condensation reaction
    • Van den Berg, H. J.; Challa, G.; Pandit, U. K. Polymer-bound thiamine models part II. Polymer effects on the catalytic activity of a macroreticular polystyrene-bound thiazolium salt in the benzoin condensation reaction. J. Mol. Cat., 1989, 51, 13-27.
    • (1989) J. Mol. Cat. , vol.51 , pp. 13-27
    • van den Berg, H.J.1    Challa, G.2    Pandit, U.K.3
  • 48
    • 0024767868 scopus 로고
    • A holoenzyme model for the thiamine dependent enzymes: Polymer catalyst supported thiazolium salt
    • Yamashita, K.; Watanabe, J. Ikeda, R.; Abe, D.; Tsuda, K. A holoenzyme model for the thiamine dependent enzymes: polymer catalyst supported thiazolium salt. Macromolecules, 1989, 22, 4392-4394.
    • (1989) Macromolecules , vol.22 , pp. 4392-4394
    • Yamashita, K.1    Watanabe, J.2    Ikeda, R.3    Abe, D.4    Tsuda, K.5
  • 49
    • 0024900396 scopus 로고
    • Acyloin condensation by polymer supported thiazolium salt: Relation between the catalytic activity and the degree of quaternization
    • Yamashita, K.; Shimizu, Y.; Tokuda, H.; Kuromiya, T.; Tsuda, K. Acyloin condensation by polymer supported thiazolium salt: relation between the catalytic activity and the degree of quaternization. J. Polym. Sci. Part A: Polym. Chem., 1989, 27, 4389-4395.
    • (1989) J. Polym. Sci. Part A: Polym. Chem. , vol.27 , pp. 4389-4395
    • Yamashita, K.1    Shimizu, Y.2    Tokuda, H.3    Kuromiya, T.4    Tsuda, K.5
  • 50
    • 0024751872 scopus 로고
    • Polymer-bound thiamine models. III. Influence of site isolation on the catalytic activity of polystyrenebound thiazolium salts
    • Van den Berg, H. J.; Challa, G.; Pandit, U. K. Polymer-bound thiamine models. III. Influence of site isolation on the catalytic activity of polystyrenebound thiazolium salts. Reac. Polym., 1989, 11, 101-116.
    • (1989) Reac. Polym. , vol.11 , pp. 101-116
    • van den Berg, H.J.1    Challa, G.2    Pandit, U.K.3
  • 51
    • 0024752963 scopus 로고
    • Polymer-bound thiamine models. IV. A simple synthetic route to immobilize a thiazolium salt to macroreticular polystyrene resins via a dimethylene spacer
    • Faber, M. C.; Challa, G.; Pandit, U. K. Polymer-bound thiamine models. IV. A simple synthetic route to immobilize a thiazolium salt to macroreticular polystyrene resins via a dimethylene spacer. Reac. Polym., 1989, 11, 117-126.
    • (1989) Reac. Polym. , vol.11 , pp. 117-126
    • Faber, M.C.1    Challa, G.2    Pandit, U.K.3
  • 52
    • 0024750678 scopus 로고
    • Polymer-bound thiamine models. V. On the stability of a macroporous polystyrene-bound thiazolium salt in the (semi)-continuous production of benzoin
    • Van den Berg, H. J.; Challa, G.; Pandit, U. K. Polymer-bound thiamine models. V. On the stability of a macroporous polystyrene-bound thiazolium salt in the (semi)-continuous production of benzoin. Reac. Polym., 1989, 11, 127-134.
    • (1989) Reac. Polym. , vol.11 , pp. 127-134
    • van den Berg, H.J.1    Challa, G.2    Pandit, U.K.3
  • 53
    • 0024631406 scopus 로고
    • Syntheses of new thiazolium salt polymers and their catalytic activities
    • Yamashita, K.; Tokuda, H.; Tsuda, K. Syntheses of new thiazolium salt polymers and their catalytic activities. J. Polym. Sci. Part A: Polym. Chem., 1989, 27, 1333-1339.
    • (1989) J. Polym. Sci. Part A: Polym. Chem. , vol.27 , pp. 1333-1339
    • Yamashita, K.1    Tokuda, H.2    Tsuda, K.3
  • 56
    • 0035300552 scopus 로고    scopus 로고
    • Effects of thiazolium counter anion and reactio media on the activity of immobilized thiazolium catalyst
    • Tajima, H.; Nütsu, T.; Inoue, H.; Ito, M. Effects of thiazolium counter anion and reactio media on the activity of immobilized thiazolium catalyst. J. Chem. Eng. Jpn., 2001, 34, 553-557.
    • (2001) J. Chem. Eng. Jpn. , vol.34 , pp. 553-557
    • Tajima, H.1    Nütsu, T.2    Inoue, H.3    Ito, M.4
  • 57
    • 4644229691 scopus 로고
    • Stetter condensation catalyzed by a polymer-bound thiazolium ylide
    • Ho, T. L.; Liu, S. H. Stetter condensation catalyzed by a polymer-bound thiazolium ylide. Synth. Commun., 1983, 13, 1125-1127.
    • (1983) Synth. Commun. , vol.13 , pp. 1125-1127
    • Ho, T.L.1    Liu, S.H.2
  • 58
    • 4644225048 scopus 로고    scopus 로고
    • ROMPgel-supported thiazolium iodide: An efficient supported organic catalyst for parallel Stetter reactions
    • Barrett, A. G. M.; Love, A. C.; Tedeschi, L. ROMPgel-supported thiazolium iodide: An efficient supported organic catalyst for parallel Stetter reactions. Org. Lett., 2004, 6, 3377-3380.
    • (2004) Org. Lett. , vol.6 , pp. 3377-3380
    • Barrett, A.G.M.1    Love, A.C.2    Tedeschi, L.3
  • 59
    • 0008874680 scopus 로고    scopus 로고
    • Immobilized triazolium salts as precursors of chiral carbenes - Rhodium-catalyzed asymmetric hydrosilylation as a first test reaction
    • Enders, D.; Gielen, H.; Breuer, K. Immobilized triazolium salts as precursors of chiral carbenes - Rhodium-catalyzed asymmetric hydrosilylation as a first test reaction. Molecules Online, 1998, 2, 105-108.
    • (1998) Molecules Online , vol.2 , pp. 105-108
    • Enders, D.1    Gielen, H.2    Breuer, K.3
  • 60
    • 52449084236 scopus 로고    scopus 로고
    • Artificial enzymes with thiazolium and imidazolium coenzyme mimics
    • Zhao, H.; Foss, F. W.; Breslow, R. Artificial enzymes with thiazolium and imidazolium coenzyme mimics. J. Am. Chem. Soc., 2008, 130, 12590-12591.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 12590-12591
    • Zhao, H.1    Foss, F.W.2    Breslow, R.3
  • 61
    • 38349109278 scopus 로고    scopus 로고
    • Organocatalysis by N-Heterocyclic carbenes
    • Enders, D.; Niemeier, O.; Henseler, A. Organocatalysis by N-Heterocyclic carbenes. Chem. Rev., 2007, 107, 5606-5655.
    • (2007) Chem. Rev. , vol.107 , pp. 5606-5655
    • Enders, D.1    Niemeier, O.2    Henseler, A.3
  • 63
    • 4143051292 scopus 로고    scopus 로고
    • Nucleophilic carbenes in asymmetric organocatalysis
    • Enders, D.; Balensiefer, T. Nucleophilic carbenes in asymmetric organocatalysis. Acc. Chem. Res., 2004, 37, 534-541.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 534-541
    • Enders, D.1    Balensiefer, T.2
  • 64
    • 84977252019 scopus 로고
    • Untersuchungen über das Radikal der Benzoesäure
    • Wöhler, F.; Liebig, J. Untersuchungen über das Radikal der Benzoesäure. Ann. Pharm., 1832, 3, 249-282.
    • (1832) Ann. Pharm. , vol.3 , pp. 249-282
    • Wöhler, F.1    Liebig, J.2
  • 65
    • 18244402611 scopus 로고
    • Reactions involving the addition of hydrogen cyanide to carbon compounds
    • Lapworth, A. Reactions involving the addition of hydrogen cyanide to carbon compounds. J. Chem. Soc. Trans., 1903, 83, 995-1005.
    • (1903) J. Chem. Soc. Trans. , vol.83 , pp. 995-1005
    • Lapworth, A.1
  • 66
    • 0000976736 scopus 로고
    • A new catalyst for acyloin condensation
    • Ukai, T.; Tanaka, R.; Dokawa, T. A new catalyst for acyloin condensation. J. Pharm. Soc. Jpn., 1943, 63, 296-300.
    • (1943) J. Pharm. Soc. Jpn. , vol.63 , pp. 296-300
    • Ukai, T.1    Tanaka, R.2    Dokawa, T.3
  • 67
    • 3142640259 scopus 로고
    • On the mechanism of thiamine action. IV. Evidence from studies on model systems
    • Breslow, R. On the mechanism of thiamine action. IV. Evidence from studies on model systems. J. Am. Chem. Soc., 1958, 80, 3719-3726.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3719-3726
    • Breslow, R.1
  • 68
    • 38949191992 scopus 로고    scopus 로고
    • Development of chiral bicyclic triazolium salt organic catalysts: The importance of the N-aryl substituent
    • Rovis, T. Development of chiral bicyclic triazolium salt organic catalysts: the importance of the N-aryl substituent. Chem. Lett., 2008, 37, 2-7.
    • (2008) Chem. Lett. , vol.37 , pp. 2-7
    • Rovis, T.1
  • 69
    • 47049097492 scopus 로고    scopus 로고
    • Synthesis of enantiopure triazolium salts from pyroglutamic acid and their evaluation in the benzoin condensation
    • Enders, D.; Han, J. Synthesis of enantiopure triazolium salts from pyroglutamic acid and their evaluation in the benzoin condensation. Tetrahedron: Asymmetry, 2008, 19, 1367-1371.
    • (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1367-1371
    • Enders, D.1    Han, J.2
  • 70
    • 46749149630 scopus 로고    scopus 로고
    • D-Camphor-derived triazolium salts for catalytic intramolecular crossed aldehyde-ketone benzoin reactions
    • Li, Y.; Feng, Z.; You, S. L. D-Camphor-derived triazolium salts for catalytic intramolecular crossed aldehyde-ketone benzoin reactions. Chem. Commun., 2008, 2263-2265.
    • (2008) Chem. Commun. , pp. 2263-2265
    • Li, Y.1    Feng, Z.2    You, S.L.3
  • 71
    • 56649122062 scopus 로고    scopus 로고
    • From mono-triazolium salt to bis-triazolium salt: Improvement of the asymmetric intermolecular bezoin condensation
    • Ma, Y.; Wei, S.; Wu, J.; Yang, F.; Liu, B.; Lan, J.; Yang, S., You, J. From mono-triazolium salt to bis-triazolium salt: Improvement of the asymmetric intermolecular bezoin condensation. Adv. Synth. Catal., 2008, 350, 2645-2651.
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 2645-2651
    • Ma, Y.1    Wei, S.2    Wu, J.3    Yang, F.4    Liu, B.5    Lan, J.6    Yang, S.7    You, J.8
  • 72
    • 38349061468 scopus 로고    scopus 로고
    • Umpolung catalysis: Assessment of catalyst and substrate reactivities in acyloin type reactions
    • Schumacher, M.; Goldfuss, B. Umpolung catalysis: assessment of catalyst and substrate reactivities in acyloin type reactions. Tetrahedron, 2008, 64, 1648-1653.
    • (2008) Tetrahedron , vol.64 , pp. 1648-1653
    • Schumacher, M.1    Goldfuss, B.2
  • 73
    • 56049084681 scopus 로고    scopus 로고
    • The mechanism of the Stetter reaction - A DFT study
    • [72] Hawkes, K. J.; Yates, B. F. The mechanism of the Stetter reaction - A DFT study. Eur. J. Org. Chem., 2008, 5563-5570.
    • (2008) Eur. J. Org. Chem. , pp. 5563-5570
    • Hawkes, K.J.1    Yates, B.F.2
  • 74
    • 70349286053 scopus 로고    scopus 로고
    • The enantioselective benzoin condensation promoted by chiral triazolium precatalysts: Stereochemical control via hydrogen bonding
    • O'Toole, S. E.; Connon, S. J. The enantioselective benzoin condensation promoted by chiral triazolium precatalysts: stereochemical control via hydrogen bonding. Org. Biomol. Chem., 2009, 7, 3584-3593.
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 3584-3593
    • O'Toole, S.E.1    Connon, S.J.2
  • 75
    • 72249111956 scopus 로고    scopus 로고
    • Highly enantioselective benzoin condensation reactions involving a bifunctional protic pentafluorophenyl-substituted triazolium precatalyst
    • Baragwanath, L.; Rose, C. A.; Zeitler, K.; Connon, S. J. Highly enantioselective benzoin condensation reactions involving a bifunctional protic pentafluorophenyl-substituted triazolium precatalyst. J. Org. Chem., 2009, 74, 9214-9217.
    • (2009) J. Org. Chem. , vol.74 , pp. 9214-9217
    • Baragwanath, L.1    Rose, C.A.2    Zeitler, K.3    Connon, S.J.4
  • 76
    • 43549123600 scopus 로고    scopus 로고
    • Synthesis of N-mesityl substituted chiral imidazolium salt for NHC-catalyzed reactions
    • Struble, J. R.; Kaeobamrung, J.; Bode, J. W. Synthesis of N-mesityl substituted chiral imidazolium salt for NHC-catalyzed reactions. Org. Lett., 2008, 10, 957-960.
    • (2008) Org. Lett. , vol.10 , pp. 957-960
    • Struble, J.R.1    Kaeobamrung, J.2    Bode, J.W.3
  • 77
    • 34547424960 scopus 로고    scopus 로고
    • Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: Synthesis of (+)- Sappanone B
    • Takikawa, H.; Suzuki, K. Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: Synthesis of (+)- Sappanone B. Org. Lett., 2007, 9, 2713-2716.
    • (2007) Org. Lett. , vol.9 , pp. 2713-2716
    • Takikawa, H.1    Suzuki, K.2
  • 78
    • 34447339639 scopus 로고    scopus 로고
    • Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcyclide precursor
    • Mennen, S. M.; Miller, S. J. Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcyclide precursor. J. Org. Chem., 2007, 72, 5260-5269.
    • (2007) J. Org. Chem. , vol.72 , pp. 5260-5269
    • Mennen, S.M.1    Miller, S.J.2
  • 79
    • 67649363846 scopus 로고    scopus 로고
    • The catalytic asymmetric intramolecular Stetter reaction
    • Read de Alaniz, J.; Rovis, T. The catalytic asymmetric intramolecular Stetter reaction. Synlett, 2009, 8, 1189-1207.
    • (2009) Synlett , vol.8 , pp. 1189-1207
    • Read de Alaniz, J.1    Rovis, T.2
  • 80
    • 41849101072 scopus 로고    scopus 로고
    • Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes
    • Read de Alaniz, J.; Kerr, M. S.; Moore, J. L.; Rovis, T. Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes. J. Org. Chem., 2008, 73, 2033-2040.
    • (2008) J. Org. Chem. , vol.73 , pp. 2033-2040
    • Read de Alaniz, J.1    Kerr, M.S.2    Moore, J.L.3    Rovis, T.4
  • 81
    • 67649506357 scopus 로고    scopus 로고
    • Enantio- and Diastereoselective intermolecular Stetter reaction of glyoxamide and alkylidene ketoamides
    • Liu, Q.; Rovis, T. Enantio- and Diastereoselective intermolecular Stetter reaction of glyoxamide and alkylidene ketoamides. Org. Lett., 2009, 11, 2856-2859.
    • (2009) Org. Lett. , vol.11 , pp. 2856-2859
    • Liu, Q.1    Rovis, T.2
  • 82
    • 54849432201 scopus 로고    scopus 로고
    • Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates
    • Liu, Q.; Perreault, S.; Rovis, T. Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates. J. Am. Chem. Soc., 2008, 130, 14066-14067.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14066-14067
    • Liu, Q.1    Perreault, S.2    Rovis, T.3
  • 83
    • 68249139769 scopus 로고    scopus 로고
    • Catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes with nitroalkenes: Backbone fluorination improves selectivity
    • DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. Catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes with nitroalkenes: Backbone fluorination improves selectivity. J. Am. Chem. Soc., 2009, 131, 10872-10874.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 10872-10874
    • Dirocco, D.A.1    Oberg, K.M.2    Dalton, D.M.3    Rovis, T.4
  • 84
    • 57549097783 scopus 로고    scopus 로고
    • Asymmetric intermolecular Stetter reactions of aromatic heterocyclic aldehydes with arylidenemalonates
    • Enders, D.; Han, J. Asymmetric intermolecular Stetter reactions of aromatic heterocyclic aldehydes with arylidenemalonates. Synthesis, 2008, 23, 3864-3868.
    • (2008) Synthesis , vol.23 , pp. 3864-3868
    • Enders, D.1    Han, J.2
  • 85
    • 52049112159 scopus 로고    scopus 로고
    • Catalytic asymmetric Stetter reaction onto vinylphosphine oxides and vinylphosphonates
    • Cullen, S. C.; Rovis, T. Catalytic asymmetric Stetter reaction onto vinylphosphine oxides and vinylphosphonates. Org. Lett., 2008, 10, 3141-4144.
    • (2008) Org. Lett. , vol.10 , pp. 3141-4144
    • Cullen, S.C.1    Rovis, T.2
  • 86
    • 73449111593 scopus 로고    scopus 로고
    • Diastereoselective synthesis of 4- hydroxytetralones via a cascade Stetter-Aldol reaction catalyzed by Nheterocyclic carbenes
    • Sun, F. G.; Huang, X. L.; Ye, S. Diastereoselective synthesis of 4- hydroxytetralones via a cascade Stetter-Aldol reaction catalyzed by Nheterocyclic carbenes. J. Org. Chem., 2010, 75, 273-276.
    • (2010) J. Org. Chem. , vol.75 , pp. 273-276
    • Sun, F.G.1    Huang, X.L.2    Ye, S.3
  • 87
    • 70349456657 scopus 로고    scopus 로고
    • Diastereoselective synthesis of indanes via a Domino Stetter-Michael addition
    • Sánchez-Larios, E.; Gravel, M. Diastereoselective synthesis of indanes via a Domino Stetter-Michael addition. J. Org. Chem., 2009, 74, 7536-7539.
    • (2009) J. Org. Chem. , vol.74 , pp. 7536-7539
    • Sánchez-Larios, E.1    Gravel, M.2
  • 88
    • 62349083420 scopus 로고    scopus 로고
    • Application of an intramolecular Stetter reaction to access trans, syn, transfused pyrans
    • McErlean, C. S. P.; Willis, A. C. Application of an intramolecular Stetter reaction to access trans, syn, transfused pyrans. Synlett, 2009, 233-236.
    • (2009) Synlett , pp. 233-236
    • McErlean, C.S.P.1    Willis, A.C.2


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