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Volumn 39, Issue 12, 2009, Pages 2178-2195

One-pot, fluoride-promoted wittig reaction

Author keywords

, unsaturated compounds; Tetra n butylammonium fluoride; Wittig reaction

Indexed keywords

ACETONITRILE DERIVATIVE; ACETOPHENONE DERIVATIVE; ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; BROMINE DERIVATIVE; BROMOACETIC ACID; COMBRETASTATIN; ESTER DERIVATIVE; FLUORIDE; PHOSPHINE DERIVATIVE; PROPIONIC ACID DERIVATIVE; TETRABUTYLAMMONIUM;

EID: 67650245759     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802654633     Document Type: Article
Times cited : (8)

References (100)
  • 1
    • 0001848341 scopus 로고
    • The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions: Stereochemistry, mechanism, and selected synthetic aspects
    • Maryanoff, B. E.; Reitz, A. B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions: Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev. 1989, 89, 863-927.
    • (1989) Chem. Rev , vol.89 , pp. 863-927
    • Maryanoff, B.E.1    Reitz, A.B.2
  • 2
    • 49549153730 scopus 로고
    • Wittig reaction in benzene-aqueous alkaline solution
    • (a) Tagaki, W.; Inoue, I.; Okonogi, T. Wittig reaction in benzene-aqueous alkaline solution. Tetrahedron Lett. 1974, 2587-2590
    • (1974) Tetrahedron Lett , pp. 2587-2590
    • Tagaki, W.1    Inoue, I.2    Okonogi, T.3
  • 3
    • 0041775346 scopus 로고
    • Synthese von 1,4-dipyridyl- und 1,4-dichinolyl-butadienen durch Wittig- synthese im zweiphasensystem.
    • (b) Hunig, S.; Stemmler, I. Synthese von 1,4-dipyridyl- und 1,4-dichinolyl-butadienen durch Wittig- synthese im zweiphasensystem. Tetrahedron Lett. 1974, 3151-3154.
    • (1974) Tetrahedron Lett , pp. 3151-3154
    • Hunig, S.1    Stemmler, I.2
  • 4
    • 0002651132 scopus 로고
    • Application of phase transfer catalysis, part 17: Wittig reactions in various two-phase systems
    • (a) Demlow, E. V.; Barahona-Naranjo, S. Application of phase transfer catalysis, part 17: Wittig reactions in various two-phase systems. J. Chem. Res. 1981, 142
    • (1981) J. Chem. Res , pp. 142
    • Demlow, E.V.1    Barahona-Naranjo, S.2
  • 5
    • 0028035338 scopus 로고    scopus 로고
    • Ding, M. W.; Shi, D. Q.; Xiao, W. J.; Huang, W. F.; Wu, T. G. Studies on the Wittig reaction, XV: A direct preparation of w-unsaturated bromides via solid/liquid transferred Wittig reactions of w-bromoalkyltriphenyl phosphonium salts with aldehydes. Synth. Commun. 1994, 24, 3235-3239
    • (b) Ding, M. W.; Shi, D. Q.; Xiao, W. J.; Huang, W. F.; Wu, T. G. Studies on the Wittig reaction, XV: A direct preparation of w-unsaturated bromides via solid/liquid transferred Wittig reactions of w-bromoalkyltriphenyl phosphonium salts with aldehydes. Synth. Commun. 1994, 24, 3235-3239
  • 6
    • 0028294365 scopus 로고
    • Synthesis of enol lactones under a solid/liquid phase transfer Witting reaction
    • (c) Jun, Z.; Kayser, M. M. Synthesis of enol lactones under a solid/liquid phase transfer Witting reaction. Synth. Commun. 1994, 24, 1179-1186
    • (1994) Synth. Commun , vol.24 , pp. 1179-1186
    • Jun, Z.1    Kayser, M.M.2
  • 7
    • 0342748354 scopus 로고    scopus 로고
    • Wittig reactions in the presence of silica gel
    • (d) Patil, V. J.; Mavers, U. Wittig reactions in the presence of silica gel. Tetrahedron Lett. 1996, 37, 1281-1284
    • (1996) Tetrahedron Lett , vol.37 , pp. 1281-1284
    • Patil, V.J.1    Mavers, U.2
  • 8
    • 0029950745 scopus 로고    scopus 로고
    • Crown ether catalyzed stereospecific synthesis of Z- and E- stilbenes by Wittig reaction in a solid-liquid two-phase system
    • (e) Bellucci, G.; Chiappe, C.; Limono, G. Crown ether catalyzed stereospecific synthesis of Z- and E- stilbenes by Wittig reaction in a solid-liquid two-phase system. Tetrahedron Lett. 1996, 37, 4225-4228.
    • (1996) Tetrahedron Lett , vol.37 , pp. 4225-4228
    • Bellucci, G.1    Chiappe, C.2    Limono, G.3
  • 9
    • 0010740126 scopus 로고
    • The reaction of carboethyoxymethylenetriphenyl- phosphorane with ketones
    • Fodor, G.; Tomoskozi, I. The reaction of carboethyoxymethylenetriphenyl- phosphorane with ketones. Tetrahedron Lett. 1961, 579-582.
    • (1961) Tetrahedron Lett , pp. 579-582
    • Fodor, G.1    Tomoskozi, I.2
  • 10
    • 0003751799 scopus 로고
    • The application of high pressure to some difficult Wittig reactions
    • Isaacs, N. S.; El-Din, G. N. The application of high pressure to some difficult Wittig reactions. Tetrahedron Lett. 1987, 28, 2191-2192.
    • (1987) Tetrahedron Lett , vol.28 , pp. 2191-2192
    • Isaacs, N.S.1    El-Din, G.N.2
  • 11
    • 0004477154 scopus 로고
    • Lithium cation-catalyzed Wittig reactions
    • See, for example, a
    • See, for example, (a) Hooper, D. L.; Garagan, S.; Kayser, M. M. Lithium cation-catalyzed Wittig reactions. J. Org. Chem. 1994, 59, 1126-1128
    • (1994) J. Org. Chem , vol.59 , pp. 1126-1128
    • Hooper, D.L.1    Garagan, S.2    Kayser, M.M.3
  • 12
    • 0000749919 scopus 로고
    • An efficient method for the preparation of alkylidenecyclopropanes
    • (b) Stafford, J. A.; McMurray, J. E. An efficient method for the preparation of alkylidenecyclopropanes. Tetrahedron Lett. 1988, 19, 2531-2534
    • (1988) Tetrahedron Lett , vol.19 , pp. 2531-2534
    • Stafford, J.A.1    McMurray, J.E.2
  • 13
    • 0027386862 scopus 로고
    • On the effect of cyclodestrin on the Z/E-selectiviy of Wittig reactions with semistabilized ylides
    • (c) Westman, G.; Wennerstrom, O.; Raston, I. On the effect of cyclodestrin on the Z/E-selectiviy of Wittig reactions with semistabilized ylides. Tetrahedron 1993, 49, 483-488.
    • (1993) Tetrahedron , vol.49 , pp. 483-488
    • Westman, G.1    Wennerstrom, O.2    Raston, I.3
  • 14
    • 0001885337 scopus 로고    scopus 로고
    • Microwave accelerated Wittig reactions of stabilized phosphorus ylides with ketones under solvent-free conditions
    • Spinella, A.; Fortunati, T.; Soriente, A. Microwave accelerated Wittig reactions of stabilized phosphorus ylides with ketones under solvent-free conditions. Synlett 1997, 93-94.
    • (1997) Synlett , pp. 93-94
    • Spinella, A.1    Fortunati, T.2    Soriente, A.3
  • 15
  • 17
    • 33746316781 scopus 로고    scopus 로고
    • One-pot Wittig reactions in water and in the presence of a surfactant
    • (a) Orsini, F.; Sello G.: Fumagalli, T. One-pot Wittig reactions in water and in the presence of a surfactant. Synlett 2006,11, 1017-1718
    • (2006) Synlett , vol.11 , pp. 1017-1718
    • Orsini, F.1    Sello, G.2    Fumagalli, T.3
  • 19
    • 85082935857 scopus 로고    scopus 로고
    • Fluoride as a base: (a) Yakobson, G. G.; Akhmetova, N. E. Alkali metal fluorides in organic synthesis. Synthesis 1983, 169-184
    • Fluoride as a base: (a) Yakobson, G. G.; Akhmetova, N. E. Alkali metal fluorides in organic synthesis. Synthesis 1983, 169-184
  • 20
    • 33847086648 scopus 로고    scopus 로고
    • Clark, J. H. Fluoride ion as a base in organic synthesis. Chem. Rev. 1980, 80, 429-452. For other types of reactions (not involving silicon-containing compounds) promoted by the fluoride anion, free or supported, see (a) Ooi, T.; Taniguchi, M.; Doda, K.; Maruoka, K. Anti-selective asymmetric synthesis of b- hydroxy-a-amino acid esters by the in situ generated chiral quaternary ammonium fluoride-catalyzed Mukaiyama-type aldol reaction. Ad. Synth. Catal. 2004, 346, 1073-1076
    • (b) Clark, J. H. Fluoride ion as a base in organic synthesis. Chem. Rev. 1980, 80, 429-452. For other types of reactions (not involving silicon-containing compounds) promoted by the fluoride anion, free or supported, see (a) Ooi, T.; Taniguchi, M.; Doda, K.; Maruoka, K. Anti-selective asymmetric synthesis of b- hydroxy-a-amino acid esters by the in situ generated chiral quaternary ammonium fluoride-catalyzed Mukaiyama-type aldol reaction. Ad. Synth. Catal. 2004, 346, 1073-1076
  • 21
    • 67049099213 scopus 로고    scopus 로고
    • KF/natural phosphate as an efficient catalyst for synthesis of 2'-hydroxychal- cones and flavanones
    • (b) Macquarrie, D. J.; Nazih, R.; Sebti, S. KF/natural phosphate as an efficient catalyst for synthesis of 2'-hydroxychal- cones and flavanones. Green Chem. 2002, 4, 56-59
    • (2002) Green Chem , vol.4 , pp. 56-59
    • Macquarrie, D.J.1    Nazih, R.2    Sebti, S.3
  • 22
    • 20344393862 scopus 로고    scopus 로고
    • Klain, T. A.; Schker- yantz, J. M. Tandem Hass-Bender/Henry reaction for the synthesis of dimethylnitro alcohols from benzylic halides. Tetrahedron Lett. 2005, 46, 4535-4538
    • (c) Klain, T. A.; Schker- yantz, J. M. Tandem Hass-Bender/Henry reaction for the synthesis of dimethylnitro alcohols from benzylic halides. Tetrahedron Lett. 2005, 46, 4535-4538
  • 23
    • 0035821262 scopus 로고    scopus 로고
    • Fluoride-promoted reactions of unsaturated carbonyl compounds: Dimerization by a non-Baylis-Hillman pathway
    • (d) Xuan, J. X.; Fry, A. J. Fluoride-promoted reactions of unsaturated carbonyl compounds: Dimerization by a non-Baylis-Hillman pathway. Tetrahedron Lett. 2001, 42, 3275-3277.
    • (2001) Tetrahedron Lett , vol.42 , pp. 3275-3277
    • Xuan, J.X.1    Fry, A.J.2
  • 24
    • 0037231022 scopus 로고    scopus 로고
    • Trialkylphosphines have been already used in Wittig reactions, in particular to enhance phosphorane reactivity when stabilized ylides were concerned: (a) Valentine, D. H.; Hillhouse, J. H. Alkyl phosphines as reagents and catalysts in organic synthesis. Synthesis 2003, 317-334
    • Trialkylphosphines have been already used in Wittig reactions, in particular to enhance phosphorane reactivity when stabilized ylides were concerned: (a) Valentine, D. H.; Hillhouse, J. H. Alkyl phosphines as reagents and catalysts in organic synthesis. Synthesis 2003, 317-334
  • 25
    • 35748959668 scopus 로고    scopus 로고
    • Synthesis of the C15-C35 segment of Chivosazole A
    • (b) Janssen, D.; Kalesse, M. Synthesis of the C15-C35 segment of Chivosazole A. Synlett 2007, 2667-2670
    • (2007) Synlett , pp. 2667-2670
    • Janssen, D.1    Kalesse, M.2
  • 26
    • 0037453686 scopus 로고    scopus 로고
    • Ortho- acylimines: A new class of chiral auxiliaries for nucleophilic addition of organolithium reagents to imines
    • (c) Boezio, A. A.; Solberghe, G.; Lauzon, C.; Charette, A. B. Ortho- acylimines: A new class of chiral auxiliaries for nucleophilic addition of organolithium reagents to imines. J. Org. Chem. 2003, 68, 3241-3245
    • (2003) J. Org. Chem , vol.68 , pp. 3241-3245
    • Boezio, A.A.1    Solberghe, G.2    Lauzon, C.3    Charette, A.B.4
  • 27
    • 34248572949 scopus 로고    scopus 로고
    • Direct and facile syntheses of heterocyclic vinyl-C- nucleosides for recognition of inverted base pairs by DNA triple helix formation: First report by direct Wittig route
    • (d) Rothman, J. H. Direct and facile syntheses of heterocyclic vinyl-C- nucleosides for recognition of inverted base pairs by DNA triple helix formation: First report by direct Wittig route. J. Org. Chem. 2007, 72, 3945-3948.
    • (2007) J. Org. Chem , vol.72 , pp. 3945-3948
    • Rothman, J.H.1
  • 28
    • 0033552259 scopus 로고    scopus 로고
    • 3aj:Appella, D. H.; Montani, I.; Shintani, R.; Ferriera, M. E.; Buchwald, L. S. Asymmetric conjugate reduction of a,b-unsaturated esters using a chiral phosphine-copper catalyst. J. Am. Chem. Soc. 1999, 121, 9473-9474.
    • 3aj:Appella, D. H.; Montani, I.; Shintani, R.; Ferriera, M. E.; Buchwald, L. S. Asymmetric conjugate reduction of a,b-unsaturated esters using a chiral phosphine-copper catalyst. J. Am. Chem. Soc. 1999, 121, 9473-9474.
  • 29
    • 0037090857 scopus 로고    scopus 로고
    • Photocrosslinkable polymers bearing pendant conjugated heterocyclic chromophores
    • Waing Fang, S.; Timpe, H. J.; Gandini, A. Photocrosslinkable polymers bearing pendant conjugated heterocyclic chromophores. Polymer 2002, 43, 3505-3510.
    • (2002) Polymer , vol.43 , pp. 3505-3510
    • Waing Fang, S.1    Timpe, H.J.2    Gandini, A.3
  • 30
    • 9744259538 scopus 로고    scopus 로고
    • Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins
    • (a) Filmon, K. F.; Delaude, L.; Demonceau, A.; Noels, A. F. Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins. Coord. Chem. Rev. 2004, 248, 2323-2336
    • (2004) Coord. Chem. Rev , vol.248 , pp. 2323-2336
    • Filmon, K.F.1    Delaude, L.2    Demonceau, A.3    Noels, A.F.4
  • 32
    • 0030979224 scopus 로고    scopus 로고
    • Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)
    • (c) Orsini, F.; Pelizzoni, F.; Bellini, B.; Miglierini, G. Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series). Carbohydr. Res. 1997, 301, 95-109
    • (1997) Carbohydr. Res , vol.301 , pp. 95-109
    • Orsini, F.1    Pelizzoni, F.2    Bellini, B.3    Miglierini, G.4
  • 33
    • 0030656388 scopus 로고    scopus 로고
    • Isolation, synthesis, and antiplatelet aggregation activity of resveratrol 3-O-b-D-gluco- pyranoside and related compound
    • (d) Orsini, F.; Pelizzoni, F.; Verotta, L.; Aburjai, T. Isolation, synthesis, and antiplatelet aggregation activity of resveratrol 3-O-b-D-gluco- pyranoside and related compound. J. Nat. Prod. 1997, 60, 1082-1087
    • (1997) J. Nat. Prod , vol.60 , pp. 1082-1087
    • Orsini, F.1    Pelizzoni, F.2    Verotta, L.3    Aburjai, T.4
  • 35
    • 0346433524 scopus 로고    scopus 로고
    • Cirla, A.; Mann, J. Combretas- tatins: From natural products to drug discovery. Nat. Prod. Rep. 2003, 20, 558-564.
    • (f) Cirla, A.; Mann, J. Combretas- tatins: From natural products to drug discovery. Nat. Prod. Rep. 2003, 20, 558-564.
  • 37
    • 33846821472 scopus 로고    scopus 로고
    • Carbon-carbon bond forming reactions with substrates absorbed non-covalently on a cellulose chromato- graphy paper support
    • (b) Hacon, J.; Morris, A.; Johnston, M.; Shanahan, S. E.; Barker, M. D.; Inglis, G. G. A.; Mcdonald, S. J. F. Carbon-carbon bond forming reactions with substrates absorbed non-covalently on a cellulose chromato- graphy paper support. Chem. Comm. 2007, 625-627
    • (2007) Chem. Comm , pp. 625-627
    • Hacon, J.1    Morris, A.2    Johnston, M.3    Shanahan, S.E.4    Barker, M.D.5    Inglis, G.G.A.6    Mcdonald, S.J.F.7
  • 39
    • 0034845974 scopus 로고    scopus 로고
    • High-pressure induced domino-Horner-Wadsworth-Emmons (HWE)- Michael reactions
    • (d) Has-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser, O. High-pressure induced domino-Horner-Wadsworth-Emmons (HWE)- Michael reactions. Synlett 2001, 1395-1398.
    • (2001) Synlett , pp. 1395-1398
    • Has-Becker, S.1    Bodmann, K.2    Kreuder, R.3    Santoni, G.4    Rein, T.5    Reiser, O.6
  • 40
    • 34250308800 scopus 로고    scopus 로고
    • Highly efficient, recyclable palladium catalyst immobilized on organic-inorganic hybrid material: Application in the Heck reaction
    • (a) Li, H.; Wang, L.; Li, P. Highly efficient, recyclable palladium catalyst immobilized on organic-inorganic hybrid material: Application in the Heck reaction. Synthesis 2007, 1635-1642
    • (2007) Synthesis , pp. 1635-1642
    • Li, H.1    Wang, L.2    Li, P.3
  • 41
    • 33947700484 scopus 로고    scopus 로고
    • A novel Heck reaction catalyzed by Co hollow nanospheres in ligand-free condition
    • (b) Zhou, P.; Li, Y.; Sun, P.; Zhou, J.; Bao, J. A novel Heck reaction catalyzed by Co hollow nanospheres in ligand-free condition. Chem. Commun. 2007, 1418-1420
    • (2007) Chem. Commun , pp. 1418-1420
    • Zhou, P.1    Li, Y.2    Sun, P.3    Zhou, J.4    Bao, J.5
  • 42
    • 33846950359 scopus 로고    scopus 로고
    • Microwave-promoted Heck reaction using Pd(OAc)2 as catalyst under ligand-free and solvent-free conditions
    • (c) Du, L. H.; Wang, Y. G. Microwave-promoted Heck reaction using Pd(OAc)2 as catalyst under ligand-free and solvent-free conditions. Synth. Commun. 2007, 37, 217-222
    • (2007) Synth. Commun , vol.37 , pp. 217-222
    • Du, L.H.1    Wang, Y.G.2
  • 43
    • 33751310387 scopus 로고    scopus 로고
    • Triethanolamine as an efficient and reusable base, ligand and reaction medium for phosphane-free palladium-catalyzed Heck reactions
    • (d) Li, J. H.; Wang, L. Triethanolamine as an efficient and reusable base, ligand and reaction medium for phosphane-free palladium-catalyzed Heck reactions. Eur. J. Org. Chem. 2006, 5099-5102
    • (2006) Eur. J. Org. Chem , pp. 5099-5102
    • Li, J.H.1    Wang, L.2
  • 44
    • 33745698740 scopus 로고    scopus 로고
    • Highly dispersed nickel and palladium nanoparticle silica aerogels: Sol-gel processing of tethered metal complexes and application as catalysts in the Mizoroki-Heck reaction
    • (e) Martinez, S.; Moreno- Mafias, M.; Vallribera, A.; Schubert, U.; Roig, A.; Molins, E. Highly dispersed nickel and palladium nanoparticle silica aerogels: Sol-gel processing of tethered metal complexes and application as catalysts in the Mizoroki-Heck reaction. New J. Chem. 2006, 1093-1097
    • (2006) New J. Chem , pp. 1093-1097
    • Martinez, S.1    Moreno- Mafias, M.2    Vallribera, A.3    Schubert, U.4    Roig, A.5    Molins, E.6
  • 45
    • 33749005084 scopus 로고    scopus 로고
    • Diatomite-supported Pd nanoparticles: An efficient catalyst for Heck and Suzuki reactions
    • (f) Zhang, Z.; Wang, Z. Diatomite-supported Pd nanoparticles: An efficient catalyst for Heck and Suzuki reactions. J. Org. Chem. 2006, 71, 7485-7487
    • (2006) J. Org. Chem , vol.71 , pp. 7485-7487
    • Zhang, Z.1    Wang, Z.2
  • 46
    • 33646465997 scopus 로고    scopus 로고
    • New N-heterocyclic carbene palladium complex/ionic liquid matrix immobilized on silica: Application as recoverable catalyst for the Heck reaction
    • (g) Karimi,B.; Enders, D. New N-heterocyclic carbene palladium complex/ionic liquid matrix immobilized on silica: Application as recoverable catalyst for the Heck reaction. Org. Lett. 2006, 8, 1237-1240
    • (2006) Org. Lett , vol.8 , pp. 1237-1240
    • Karimi, B.1    Enders, D.2
  • 47
    • 20544475233 scopus 로고    scopus 로고
    • CuI/Dabco as a highly active catalytic system for the Heck-type reaction
    • (h) Li, J. H.; Wang, D. P.; Xie, Y. X. CuI/Dabco as a highly active catalytic system for the Heck-type reaction. Tetrahedron Lett. 2005, 46, 4941-4944
    • (2005) Tetrahedron Lett , vol.46 , pp. 4941-4944
    • Li, J.H.1    Wang, D.P.2    Xie, Y.X.3
  • 49
    • 33746216295 scopus 로고    scopus 로고
    • Catalysis in capillaries by Pd thin films using microwave-assisted continuous- flow organic synthesis (MACOS)
    • (l) Shore, G.; Morin, S.; Organ, M. G. Catalysis in capillaries by Pd thin films using microwave-assisted continuous- flow organic synthesis (MACOS). Angew. Chem., Int. Ed. 2006, 45, 2761-2766
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 2761-2766
    • Shore, G.1    Morin, S.2    Organ, M.G.3
  • 50
    • 25844476804 scopus 로고    scopus 로고
    • Tetraarylpho- sphonium halides as arylating reagents in Pd-catalyzed Heck and cross-coupling reactions
    • (m) Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Tetraarylpho- sphonium halides as arylating reagents in Pd-catalyzed Heck and cross-coupling reactions. Angew. Chem. Int. Ed. 2005, 44, 6166-6169
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6166-6169
    • Hwang, L.K.1    Na, Y.2    Lee, J.3    Do, Y.4    Chang, S.5
  • 51
    • 28844491607 scopus 로고    scopus 로고
    • Electrochemically assisted Heck reactions
    • (n) Tian, J.; Moeller, K. D. Electrochemically assisted Heck reactions. Org. Lett. 2005, 7, 5381-5383
    • (2005) Org. Lett , vol.7 , pp. 5381-5383
    • Tian, J.1    Moeller, K.D.2
  • 52
    • 18844441426 scopus 로고    scopus 로고
    • Palladium-catalyzed intermolecular three- component coupling of aryl iodides, alkynes, and alkenes to produce 1,3- butadiene derivatives
    • (o) Shibata, K.; Satoh, T.; Miura, M. Palladium-catalyzed intermolecular three- component coupling of aryl iodides, alkynes, and alkenes to produce 1,3- butadiene derivatives. Org. Lett. 2005, 7, 1781-1783.
    • (2005) Org. Lett , vol.7 , pp. 1781-1783
    • Shibata, K.1    Satoh, T.2    Miura, M.3
  • 53
    • 33645925672 scopus 로고    scopus 로고
    • Air-stable, phosphine-free anionic palladacyclopentadienyl catalysts: Remarkable halide and pseudohalide effects in Stille coupling
    • Crawforth, C. M.; Fairlamb, I. J. S.; Kapdi, A. R.; Serrano, J. L.; Taylor, R. J. K.; Sanchez, G. Air-stable, phosphine-free anionic palladacyclopentadienyl catalysts: Remarkable halide and pseudohalide effects in Stille coupling. Adv. Synth. Catal. 2006, 348, 405-412.
    • (2006) Adv. Synth. Catal , vol.348 , pp. 405-412
    • Crawforth, C.M.1    Fairlamb, I.J.S.2    Kapdi, A.R.3    Serrano, J.L.4    Taylor, R.J.K.5    Sanchez, G.6
  • 54
    • 0030047732 scopus 로고    scopus 로고
    • Guevel, A. C.; Hart, D. J. Synthesis ofcarbocycles via intramolecular conjugate additions: Another solution to the terpenoid side chain stereochemistry problem. J. Org. Chem. 1996, 61, 465-472.
    • Guevel, A. C.; Hart, D. J. Synthesis ofcarbocycles via intramolecular conjugate additions: Another solution to the terpenoid side chain stereochemistry problem. J. Org. Chem. 1996, 61, 465-472.
  • 55
    • 34250211446 scopus 로고    scopus 로고
    • The first sequential reaction promoted by manganese: Complete stereoselective synthesis of (E)-aα,bβ-unsaturated esters from 2,2-dichloroesters and aldehydes
    • Concellon, J. M.; Rodriguez-Solla, H.; Diaz, P.; Llavona, R. The first sequential reaction promoted by manganese: Complete stereoselective synthesis of (E)-aα,bβ-unsaturated esters from 2,2-dichloroesters and aldehydes. J. Org. Chem. 2007, 72, 4396-4400.
    • (2007) J. Org. Chem , vol.72 , pp. 4396-4400
    • Concellon, J.M.1    Rodriguez-Solla, H.2    Diaz, P.3    Llavona, R.4
  • 56
    • 0030566869 scopus 로고    scopus 로고
    • Chiral dienolate chemistry in remote asymmetric induction: The asymmetric aldol/oxycope strategy for asymmetric synthesis of yγ,δ-dichiral aα,bβ-unsaturated acid derivatives
    • Tamooka, K.; Nagasawa, A.; Wie, S.; Nakai, T. Chiral dienolate chemistry in remote asymmetric induction: The asymmetric aldol/oxycope strategy for asymmetric synthesis of yγ,δ-dichiral aα,bβ-unsaturated acid derivatives. Tetrahedron Lett. 1996, 37, 8899-8900.
    • (1996) Tetrahedron Lett , vol.37 , pp. 8899-8900
    • Tamooka, K.1    Nagasawa, A.2    Wie, S.3    Nakai, T.4
  • 58
    • 33644764723 scopus 로고    scopus 로고
    • Stereoselective synthesis of (E)-aα,bβ-unsaturated esters via carbene- catalyzed redox esterification
    • Zeitler, K. Stereoselective synthesis of (E)-aα,bβ-unsaturated esters via carbene- catalyzed redox esterification. Org. Lett. 2006, 8, 637-640.
    • (2006) Org. Lett , vol.8 , pp. 637-640
    • Zeitler, K.1
  • 59
    • 28944451360 scopus 로고    scopus 로고
    • A practical, efficient, and atom economic alternative to the Wittig and Horner- Wadsworth-Emmons reactions for the synthesis of(E)-a,b-unsaturated esters from aldehydes
    • (a) List, B.; Doehring, A.; Fonseca, M. T. H.; Job, A.; Torres, R. R. A practical, efficient, and atom economic alternative to the Wittig and Horner- Wadsworth-Emmons reactions for the synthesis of(E)-a,b-unsaturated esters from aldehydes. Tetrahedron 2006, 62, 476-482
    • (2006) Tetrahedron , vol.62 , pp. 476-482
    • List, B.1    Doehring, A.2    Fonseca, M.T.H.3    Job, A.4    Torres, R.R.5
  • 60
    • 0000435980 scopus 로고    scopus 로고
    • Excellent Z-selective olefin formation using pentacoordinate spirophosphoranes and aldehydes: Wittig-type reaction via hexacoordinate intermediates
    • (b) Kojima, S.; Takagi, R.; Akiba, K. Excellent Z-selective olefin formation using pentacoordinate spirophosphoranes and aldehydes: Wittig-type reaction via hexacoordinate intermediates. J. Am. Chem. Soc. 1997, 119, 5970-5971
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 5970-5971
    • Kojima, S.1    Takagi, R.2    Akiba, K.3
  • 61
    • 84985294565 scopus 로고
    • Uber die Anwendung von hohem druck bei Wittig-reaktionen mit resonanzstabilisierten yliden.
    • (c) Nonnenmacher, A.; Mayer, R.; Plieniger, H. Uber die Anwendung von hohem druck bei Wittig-reaktionen mit resonanzstabilisierten yliden. Liebigs. Ann. Chem. 1983, 2135-2140
    • (1983) Liebigs. Ann. Chem , pp. 2135-2140
    • Nonnenmacher, A.1    Mayer, R.2    Plieniger, H.3
  • 62
    • 0029004173 scopus 로고
    • The Wittig reaction of stable ylide with aldehyde under microway irradiation: Synthesis of ethyl cinnamates
    • (d) Xu, C.; Chen, G.; Fu, C.; Huang, X. The Wittig reaction of stable ylide with aldehyde under microway irradiation: Synthesis of ethyl cinnamates. Synth. Commun. 1995, 25, 2229-2233.
    • (1995) Synth. Commun , vol.25 , pp. 2229-2233
    • Xu, C.1    Chen, G.2    Fu, C.3    Huang, X.4
  • 63
    • 0000302952 scopus 로고    scopus 로고
    • Horner- Emmons synthesis with minimal purification using ROMPGEL: A novel high-loading matrix for supported reagents
    • (a) Barrett, A. G. M.; Cramp, S. M.; Roberts, S. R.; Zecri, F. J. Horner- Emmons synthesis with minimal purification using ROMPGEL: A novel high-loading matrix for supported reagents. Org. Lett. 1999, 1, 579-582
    • (1999) Org. Lett , vol.1 , pp. 579-582
    • Barrett, A.G.M.1    Cramp, S.M.2    Roberts, S.R.3    Zecri, F.J.4
  • 64
    • 0001562872 scopus 로고
    • Reactions of 3-hydroxyvinyl selenones with alkoxides: Oxetane formation and fragmentation reactions
    • (b) Makoto, S.; Ryoichi, A.; Isao, K. Reactions of 3-hydroxyvinyl selenones with alkoxides: Oxetane formation and fragmentation reactions. J. Org. Chem. 1984, 149, 1230-1238.
    • (1984) J. Org. Chem , vol.149 , pp. 1230-1238
    • Makoto, S.1    Ryoichi, A.2    Isao, K.3
  • 65
    • 0037221407 scopus 로고    scopus 로고
    • Tandem Michael-Wittig-Horner reaction: Application to the synthesis of bisabolanes
    • (a) Chuzel, O.; Piva, O. Tandem Michael-Wittig-Horner reaction: Application to the synthesis of bisabolanes. Synth. Commun. 2003, 33, 393-402;
    • (2003) Synth. Commun , vol.33 , pp. 393-402
    • Chuzel, O.1    Piva, O.2
  • 66
    • 18744396076 scopus 로고    scopus 로고
    • Wittig reactions of stabilized phosphorus ylides with aldehydes in water
    • (b) Wu, J.; Zhang, D.; Wie, S. Wittig reactions of stabilized phosphorus ylides with aldehydes in water. Synth. Commun. 2005, 35, 1213-1222
    • (2005) Synth. Commun , vol.35 , pp. 1213-1222
    • Wu, J.1    Zhang, D.2    Wie, S.3
  • 67
    • 67650246225 scopus 로고    scopus 로고
    • see Ref. 1
    • (c) see Ref. 1.
  • 68
    • 67650252363 scopus 로고    scopus 로고
    • See Ref. 3a
    • (a) See Ref. 3a
  • 69
    • 33748346898 scopus 로고
    • Methyltrioxorhenium as catalyst of a novel aldehyde olefination
    • (b) Herrman, W. A.; Mei, W. Methyltrioxorhenium as catalyst of a novel aldehyde olefination. Angew. Chem. Int. Ed. Engl. 1991, 30, 1641-1643
    • (1991) Angew. Chem. Int. Ed. Engl , vol.30 , pp. 1641-1643
    • Herrman, W.A.1    Mei, W.2
  • 70
    • 33644690153 scopus 로고    scopus 로고
    • Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions
    • (c) Artuso, E.; Barbero, M.; Degani, J.; Sughera, S.; Fochi, R. Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions. Tetrahedron 2006, 3146-3157.
    • (2006) Tetrahedron , pp. 3146-3157
    • Artuso, E.1    Barbero, M.2    Degani, J.3    Sughera, S.4    Fochi, R.5
  • 71
    • 0035953320 scopus 로고    scopus 로고
    • Novel seco cyclopropa[c]pyrrolo[3,2-e]indole isalkylators bearing a 3,3'-arylenebisa- cryloyl group as a clinker
    • Fukuda, Y.; Seto, S.; Furuta, H.; Ebisu, H.; Omori, Y.; Terashima, S. Novel seco cyclopropa[c]pyrrolo[3,2-e]indole isalkylators bearing a 3,3'-arylenebisa- cryloyl group as a clinker. J. Med. Chem. 2001, 44, 1396-1406.
    • (2001) J. Med. Chem , vol.44 , pp. 1396-1406
    • Fukuda, Y.1    Seto, S.2    Furuta, H.3    Ebisu, H.4    Omori, Y.5    Terashima, S.6
  • 72
    • 1642588238 scopus 로고    scopus 로고
    • New solid-supported phosphonate reagents for the synthesis of Z-aα,bβ-unsaturated esters
    • (a) Martina, S. L. X.; Taylor, R. J. K. New solid-supported phosphonate reagents for the synthesis of Z-aα,bβ-unsaturated esters. Tetrahedron Lett. 2004, 45, 3279-3282
    • (2004) Tetrahedron Lett , vol.45 , pp. 3279-3282
    • Martina, S.L.X.1    Taylor, R.J.K.2
  • 73
    • 0141615958 scopus 로고    scopus 로고
    • Gold-catalyzed hydroar- ylation of alkynes
    • (b) Reetz, M. T.; Sommer, K. Gold-catalyzed hydroar- ylation of alkynes. Eur. J. Org. Chem. 2003, 3485-3496
    • (2003) Eur. J. Org. Chem , pp. 3485-3496
    • Reetz, M.T.1    Sommer, K.2
  • 74
    • 67650240262 scopus 로고    scopus 로고
    • See Ref. 3b
    • (c) See Ref. 3b.
  • 75
    • 20444471585 scopus 로고    scopus 로고
    • Synthesis, biological activity, and modelling studies of two novel anti-HIV PR inhibitors with a thiophene containing hydroxyethylamino core
    • (a) Bonini, C., Chiummiento, L.; De Bonis, M.; Funicello, M.; Lupattelli, P.; Suanno, G.; Berti, F.; Campaner, P. Synthesis, biological activity, and modelling studies of two novel anti-HIV PR inhibitors with a thiophene containing hydroxyethylamino core. Tetrahedron 2005, 61, 6580-6589
    • (2005) Tetrahedron , vol.61 , pp. 6580-6589
    • Bonini, C.1    Chiummiento, L.2    De Bonis, M.3    Funicello, M.4    Lupattelli, P.5    Suanno, G.6    Berti, F.7    Campaner, P.8
  • 76
    • 84952382019 scopus 로고
    • P.aα-Lithioalkylphosphonates as functional group carriers: An in situ acrylic esters synthesis
    • (b) Tay, M. K.; About-Joudet, E.; Callignon, N.; Teulade, M. P.; Savignac, P.aα-Lithioalkylphosphonates as functional group carriers: An in situ acrylic esters synthesis. Synth. Commun. 1988, 18, 1349-1362
    • (1988) Synth. Commun , vol.18 , pp. 1349-1362
    • Tay, M.K.1    About-Joudet, E.2    Callignon, N.3    Teulade, M.P.4    Savignac5
  • 77
    • 20644465595 scopus 로고    scopus 로고
    • Synthesis, characterization, and photocross-linking of copolymers of furan and aliphatic hydroxyethylesters prepared by transesterification
    • (a) Lassaeuguette, E.; Gandini, A.; Belgacem, M. N.; Timpe, H. J. Synthesis, characterization, and photocross-linking of copolymers of furan and aliphatic hydroxyethylesters prepared by transesterification. Polymer 2005, 46, 5476-5483
    • (2005) Polymer , vol.46 , pp. 5476-5483
    • Lassaeuguette, E.1    Gandini, A.2    Belgacem, M.N.3    Timpe, H.J.4
  • 79
    • 0001589965 scopus 로고
    • Conversion of aα,bβ-unsaturated esters to their ß,γ- unsaturated isomers by photochemical deconjugation
    • (a) Duhaime, R. M.; Lombardo, D. A.; Skinner, I. A.; Weedon, A. C. Conversion of aα,bβ-unsaturated esters to their ß,γ- unsaturated isomers by photochemical deconjugation. J. Org. Chem. 1985, 50, 873-879
    • (1985) J. Org. Chem , vol.50 , pp. 873-879
    • Duhaime, R.M.1    Lombardo, D.A.2    Skinner, I.A.3    Weedon, A.C.4
  • 80
    • 84986366131 scopus 로고
    • Diastereoface selectivity during phthalimidonitrene additions to (E)- and (Z)-configurated aα,bβ- unsaturated esters, induced by a chiral center in the y-position
    • (b) Chilmonczyk, Z.; Egli, M.; Behringcr, C.; Dreiding, A. S. Diastereoface selectivity during phthalimidonitrene additions to (E)- and (Z)-configurated aα,bβ- unsaturated esters, induced by a chiral center in the y-position. Helv. Chim. Acta 1989, 72, 1095-1116
    • (1989) Helv. Chim. Acta , vol.72 , pp. 1095-1116
    • Chilmonczyk, Z.1    Egli, M.2    Behringcr, C.3    Dreiding, A.S.4
  • 81
    • 0001324553 scopus 로고
    • A convenient synthesis of L-(S)-glyceraldehyde acetonide from L-ascorbic acid
    • (c) Hubschwerlein, C. A convenient synthesis of L-(S)-glyceraldehyde acetonide from L-ascorbic acid. Synthesis 1986, 962-964
    • (1986) Synthesis , pp. 962-964
    • Hubschwerlein, C.1
  • 82
    • 84987166703 scopus 로고
    • Practical synthesis of some versatile chiral building blocks from (D)-mannitol
    • (d) Takano, S.; Kurotaki, A.; Takahashi, M.; Ogasawara, K. Practical synthesis of some versatile chiral building blocks from (D)-mannitol. Synthesis 1986, 403-406.
    • (1986) Synthesis , pp. 403-406
    • Takano, S.1    Kurotaki, A.2    Takahashi, M.3    Ogasawara, K.4
  • 83
    • 0035114846 scopus 로고    scopus 로고
    • Improved Horner-Wadsworth-Emmons preparation of α-methyl or aα-ethyl-aα,P-unsaturated esters from aldehydes
    • (a) Petroski, R. J.; Weisleder, D. Improved Horner-Wadsworth-Emmons preparation of α-methyl or aα-ethyl-aα,P-unsaturated esters from aldehydes. Synth. Commun. 2001, 31, 89-95
    • (2001) Synth. Commun , vol.31 , pp. 89-95
    • Petroski, R.J.1    Weisleder, D.2
  • 84
    • 0032514965 scopus 로고    scopus 로고
    • Ando K. Z-Selective Horner- Wadsworth-Emmons reaction of aα-substituted ethyl (diarylphosphono) acetates with aldehydes. J. Org. Chem. 1998, 63, 8411-8416.
    • (b) Ando K. Z-Selective Horner- Wadsworth-Emmons reaction of aα-substituted ethyl (diarylphosphono) acetates with aldehydes. J. Org. Chem. 1998, 63, 8411-8416.
  • 85
    • 0032480397 scopus 로고    scopus 로고
    • Mn(III)-based oxidative free-radical 6-endo cyclizations of Z-trisubstituted alkenes
    • Snider, B. B.; Kiselgof, J. Y. Mn(III)-based oxidative free-radical 6-endo cyclizations of Z-trisubstituted alkenes. Tetrahedron 1998, 54, 10641-10648.
    • (1998) Tetrahedron , vol.54 , pp. 10641-10648
    • Snider, B.B.1    Kiselgof, J.Y.2
  • 86
    • 67650228158 scopus 로고    scopus 로고
    • Dambacher, J, Zhao, W, El-Batta, A, Anness, R, Jiang, C, Bergdahl, M. Water is an efficient medium for Wittig reactions employing stabilized
    • (a) Dambacher, J.; Zhao, W.; El-Batta, A.; Anness, R.; Jiang, C.; Bergdahl, M. Water is an efficient medium for Wittig reactions employing stabilized
  • 87
    • 19544381844 scopus 로고    scopus 로고
    • ylides and aldehyde. Tetrahedron Lett. 2005, 46, 4473-4477
    • ylides and aldehyde. Tetrahedron Lett. 2005, 46, 4473-4477
  • 88
    • 33744820319 scopus 로고    scopus 로고
    • Convenient stereoselective synthesis of(Z)-chalcone derivatives from 1,3-diaryl-2-propynyl silyl ethers
    • (b) Yoshizawa, K.; Shioiri, T. Convenient stereoselective synthesis of(Z)-chalcone derivatives from 1,3-diaryl-2-propynyl silyl ethers. Tetrahedron Lett. 2006, 4943-4945
    • (2006) Tetrahedron Lett , pp. 4943-4945
    • Yoshizawa, K.1    Shioiri, T.2
  • 89
    • 11244272872 scopus 로고    scopus 로고
    • Efficient coupling of arylalkanes and aldehydes leading to the synthesis of enones
    • (c) Li- Wen, X.; Lyi, L.; Chun-Gu, X.; Pei-Qing, Z. Efficient coupling of arylalkanes and aldehydes leading to the synthesis of enones. Helv. Chim. Acta 2004, 87, 3080-3084
    • (2004) Helv. Chim. Acta , vol.87 , pp. 3080-3084
    • Li- Wen, X.1    Lyi, L.2    Chun-Gu, X.3    Pei-Qing, Z.4
  • 90
    • 67650273455 scopus 로고    scopus 로고
    • Budavari, S. (Ed.). The Merck Index, 12th, Ed.; Merck & Co.; Whitehouse Station, NJ, 1996.
    • (d) Budavari, S. (Ed.). The Merck Index, 12th, Ed.; Merck & Co.; Whitehouse Station, NJ, 1996.
  • 91
    • 16844364568 scopus 로고    scopus 로고
    • Rhodium-catalyzed acylation of vinylsilanes with acid anhydrides
    • (a) Yamane, M.; Uera, K.; Narasaka, K. Rhodium-catalyzed acylation of vinylsilanes with acid anhydrides. Bull. Chem. Soc. Jpn. 2005, 78, 477-486
    • (2005) Bull. Chem. Soc. Jpn , vol.78 , pp. 477-486
    • Yamane, M.1    Uera, K.2    Narasaka, K.3
  • 92
    • 21644446264 scopus 로고    scopus 로고
    • Application of organocerium reagents for the efficient conversion of Z-a,b-unsaturated Weinreb amides to Z-a,b-unsaturated ketones
    • (b) Kojima, S.; Hidaka, T.; Yamakawa, A. Application of organocerium reagents for the efficient conversion of Z-a,b-unsaturated Weinreb amides to Z-a,b-unsaturated ketones. Chem. Lett. 2005, 34, 470-471.
    • (2005) Chem. Lett , vol.34 , pp. 470-471
    • Kojima, S.1    Hidaka, T.2    Yamakawa, A.3
  • 93
    • 0036033016 scopus 로고    scopus 로고
    • Stereoselective synthesis of (E)- cinnamonitriles via Heck arylation of acrylonitrile and aryl iodides in water
    • (a) Zhao, H.; Cai, M.-Z.; Peng, C. Y. Stereoselective synthesis of (E)- cinnamonitriles via Heck arylation of acrylonitrile and aryl iodides in water. Synth. Commun. 2002, 32, 3419-3423
    • (2002) Synth. Commun , vol.32 , pp. 3419-3423
    • Zhao, H.1    Cai, M.-Z.2    Peng, C.Y.3
  • 95
    • 0001357759 scopus 로고
    • Synthesis of 2,2'-diacyl-1,1'-biaryls. Regiocon- trolled protection of ketones in unsymmetrically substituted 9,10-phenanthre- nequinones
    • (a) Mervic, M.; Ghera, E. Synthesis of 2,2'-diacyl-1,1'-biaryls. Regiocon- trolled protection of ketones in unsymmetrically substituted 9,10-phenanthre- nequinones. J. Org. Chem. 1980, 45, 4720-4725
    • (1980) J. Org. Chem , vol.45 , pp. 4720-4725
    • Mervic, M.1    Ghera, E.2
  • 96
    • 0026047751 scopus 로고
    • Synthesis and evaluation ofstilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
    • (b) Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin, C. M.; Hamel, E. Synthesis and evaluation ofstilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J. Med. Chem. 1991, 34, 2579-2588
    • (1991) J. Med. Chem , vol.34 , pp. 2579-2588
    • Cushman, M.1    Nagarathnam, D.2    Gopal, D.3    Chakraborti, A.K.4    Lin, C.M.5    Hamel, E.6
  • 98
    • 0031053263 scopus 로고    scopus 로고
    • Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules
    • (a) Alonso, E.; Ramon, J. D.; Yus, M. Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules. J. Org. Chem. 1997, 62, 417-421
    • (1997) J. Org. Chem , vol.62 , pp. 417-421
    • Alonso, E.1    Ramon, J.D.2    Yus, M.3
  • 99
    • 0023801309 scopus 로고
    • Interaction of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: A structure-activity study
    • (b) Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.; Schmidt, J. M.; Pettit, G. R.; Hamel, E. Interaction of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: A structure-activity study. Mol. Pharmacol. 1988, 34, 200-208
    • (1988) Mol. Pharmacol , vol.34 , pp. 200-208
    • Lin, C.M.1    Singh, S.B.2    Chu, P.S.3    Dempcy, R.O.4    Schmidt, J.M.5    Pettit, G.R.6    Hamel, E.7
  • 100
    • 0025804962 scopus 로고
    • Quantitative structure-activity relationship analysis of combretastatins: A class of novel antimitotic agents
    • (c) Nandy, P.;Banerjee, S.; Gao, H.; Hui, M. B. V.; Lien, E. Quantitative structure-activity relationship analysis of combretastatins: A class of novel antimitotic agents. J. Pharm. Res. 1991, 8, 776-781.
    • (1991) J. Pharm. Res , vol.8 , pp. 776-781
    • Nandy, P.1    Banerjee, S.2    Gao, H.3    Hui, M.B.V.4    Lien, E.5


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