메뉴 건너뛰기




Volumn 19, Issue 2, 2014, Pages 1763-1774

Pauson-Khand reaction of internal dissymmetric trifluoromethyl alkynes. Influence of the alkene on the regioselectivity

Author keywords

Cycloadditions; Cyclopentenones; Pauson Khand reaction; Regioselectivity; Trifluoromethylalkynes

Indexed keywords

ALKYNE; ETHYLENE; ETHYLENE DERIVATIVE; FLUORINATED HYDROCARBON; NORBORNANE DERIVATIVE; TRIFLUOROMETHYL HYPOFLUORITE;

EID: 84894625138     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19021763     Document Type: Article
Times cited : (8)

References (25)
  • 2
    • 67650317689 scopus 로고    scopus 로고
    • Synthesis of prostaglandin and phytoprostane b1 via regioselective intermolecular pauson-khand reactions
    • Vazquez-Romero, A.; Cardenas, L.; Blasi, E.; Verdaguer, X.; Riera, A. Synthesis of Prostaglandin and Phytoprostane B1 Via Regioselective Intermolecular Pauson-Khand Reactions. Org. Lett. 2009, 11, 3104-3107.
    • (2009) Org. Lett. , vol.11 , pp. 3104-3107
    • Vazquez-Romero, A.1    Cardenas, L.2    Blasi, E.3    Verdaguer, X.4    Riera, A.5
  • 3
    • 33747883758 scopus 로고    scopus 로고
    • First c-c bond formation in the pauson-khand reaction: Influence of carbon-carbon triple bond polarization on regiochemistry
    • De Bruin, T.J.M.; Michel, C.; Vekey, K.; Greene, A.E.; Gimbert, Y.; Milet, A. First C-C bond formation in the Pauson-Khand reaction: Influence of carbon-carbon triple bond polarization on regiochemistry. J. Organomet. Chem. 2006, 691, 4281-4288.
    • (2006) J. Organomet. Chem. , vol.691 , pp. 4281-4288
    • De Bruin, T.J.M.1    Michel, C.2    Vekey, K.3    Greene, A.E.4    Gimbert, Y.5    Milet, A.6
  • 4
    • 0034835790 scopus 로고    scopus 로고
    • Theoretical study of the regiochemistry-determining step of the pauson-khand reaction
    • De Bruin, T.J.M.; Milet, A.; Robert, F.; Gimbert, Y.; Greene, A.E. Theoretical Study of the Regiochemistry-Determining Step of the Pauson-Khand Reaction. J. Am. Chem. Soc. 2001, 123, 7184-7185.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7184-7185
    • De Bruin, T.J.M.1    Milet, A.2    Robert, F.3    Gimbert, Y.4    Greene, A.E.5
  • 5
    • 0034827269 scopus 로고    scopus 로고
    • Regiochemistry in the pauson-khand reaction: Has a trans effect been overlooked?
    • Robert, F.; Milet, A.; Gimbert, Y.; Konya, D.; Greene, A. E. Regiochemistry in the Pauson-Khand Reaction: Has a Trans Effect Been Overlooked? J. Am. Chem. Soc. 2001, 123, 5396-5400.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5396-5400
    • Robert, F.1    Milet, A.2    Gimbert, Y.3    Konya, D.4    Greene, A.E.5
  • 6
    • 84867705580 scopus 로고    scopus 로고
    • Electronic regioselectivity of diarylalkynes in cobalt-mediated pausond-khand reaction: An experimental and computational study with para- and meta-substituted diarylalkynes and norbornene
    • Fager-Jokela, E.; Muuronen, M.; Patzschke, M.; Helaja, J. Electronic Regioselectivity of Diarylalkynes in Cobalt-Mediated Pausond-Khand Reaction: An Experimental and Computational Study with Para- and Meta-Substituted Diarylalkynes and Norbornene. J. Org. Chem. 2012, 77, 9134-9147.
    • (2012) J. Org. Chem. , vol.77 , pp. 9134-9147
    • Fager-Jokela, E.1    Muuronen, M.2    Patzschke, M.3    Helaja, J.4
  • 7
    • 79959663217 scopus 로고    scopus 로고
    • Regiochemistry in cobalt-mediated intermolecular pauson-khand reactions of unsymmetrical internal heteroaromatic alkynes with norbornene
    • Moulton, B.E.; Whitwood, A.C.; Duhme-Klair, A.K.; Lynam, J.M.; Fairlamb, I.J.S. Regiochemistry in cobalt-mediated intermolecular Pauson-Khand reactions of unsymmetrical internal heteroaromatic alkynes with norbornene. J. Org. Chem. 2011, 76, 5320-5334.
    • (2011) J. Org. Chem. , vol.76 , pp. 5320-5334
    • Moulton, B.E.1    Whitwood, A.C.2    Duhme-Klair, A.K.3    Lynam, J.M.4    Fairlamb, I.J.S.5
  • 8
    • 78650340324 scopus 로고    scopus 로고
    • Regioselectivity in intermolecular pauson-khand reactions of dissymmetric fluorinated alkynes
    • Kizirian, J.; Aiguabella, N.; Pesquer, A.; Fustero, S.; Bello, P.; Verdaguer, X.; Riera, A. Regioselectivity in Intermolecular Pauson-Khand Reactions of Dissymmetric Fluorinated Alkynes. Org. Lett. 2010, 12, 5620-5623.
    • (2010) Org. Lett. , vol.12 , pp. 5620-5623
    • Kizirian, J.1    Aiguabella, N.2    Pesquer, A.3    Fustero, S.4    Bello, P.5    Verdaguer, X.6    Riera, A.7
  • 9
    • 84877270612 scopus 로고    scopus 로고
    • Synthesis and application of β- substituted pauson-khand adducts: Trifluoromethyl as a removable steering group
    • Aiguabella, N.; del Pozo, C.; Verdaguer, X.; Fustero, S.; Riera, A. Synthesis and Application of β- Substituted Pauson-Khand Adducts: Trifluoromethyl as a Removable Steering Group. Angew. Chem. Int. Ed. 2013, 52, 5355-5359.
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 5355-5359
    • Aiguabella, N.1    Del Pozo, C.2    Verdaguer, X.3    Fustero, S.4    Riera, A.5
  • 10
    • 9444248521 scopus 로고    scopus 로고
    • thesis, Reactivity, Applications; Wiley-VCH: Weinheim, Germany
    • Peer, K. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Modern Fluoroorganic Chemistry: Syn
    • Peer, K.1
  • 11
    • 84874743947 scopus 로고    scopus 로고
    • Direct trifluoromethylation of the c-h bond
    • Liu, H.; Gu, Z.; Jiang, X. Direct Trifluoromethylation of the C-H Bond. Adv. Synth. Catal. 2013, 355, 617-626.
    • (2013) Adv. Synth. Catal. , vol.355 , pp. 617-626
    • Liu, H.1    Gu, Z.2    Jiang, X.3
  • 12
    • 84882268052 scopus 로고    scopus 로고
    • Introduction of fluorine and fluorine-containing functional groups
    • Liang, T.; Neumann, C.N.; Ritter, T. Introduction of Fluorine and Fluorine-Containing Functional Groups. Angew. Chem. Int. Ed. 2013, 52, 8214-8264.
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 8214-8264
    • Liang, T.1    Neumann, C.N.2    Ritter, T.3
  • 13
    • 52149087002 scopus 로고    scopus 로고
    • Selective enhancement effects of silver salts on the transition metal-catalyzed synthesis of gem-difluorinated heterocyclics using 2,2- difluorohomopropargyl amides
    • Arimitsu, S.; Bottom, R.L.; Hammond, G.B. Selective enhancement effects of silver salts on the transition metal-catalyzed synthesis of gem-difluorinated heterocyclics using 2,2- difluorohomopropargyl amides. J. Fluorine Chem. 2008, 129, 1047-1051.
    • (2008) J. Fluorine Chem. , vol.129 , pp. 1047-1051
    • Arimitsu, S.1    Bottom, R.L.2    Hammond, G.B.3
  • 14
    • 17144388221 scopus 로고    scopus 로고
    • Synthesis of alpha-trifluoromethylated nitrogen bicycles
    • Ferry, A.; Billard, T.; Langlois, B.R. Synthesis of alpha- Trifluoromethylated nitrogen bicycles. Synlett 2005, 1027-1029.
    • (2005) Synlett , pp. 1027-1029
    • Ferry, A.1    Billard, T.2    Langlois, B.R.3
  • 15
    • 23944493189 scopus 로고    scopus 로고
    • Towards the syntheses of alpha-trifluoromethylated oxygenated heterocycles and their precursors
    • Harthong, S.; Billard, T.; Langlois, B.R. Towards the syntheses of alpha-trifluoromethylated oxygenated heterocycles and their precursors. Synthesis 2005, 2253-2263.
    • (2005) Synthesis , pp. 2253-2263
    • Harthong, S.1    Billard, T.2    Langlois, B.R.3
  • 16
    • 0034840336 scopus 로고    scopus 로고
    • Scope and limitation of intramolecular pauson-khand reaction of fluorine-containing enynes
    • Ishizaki, M.; Suzuki, D.; Hoshino, O. Scope and limitation of intramolecular Pauson-Khand reaction of fluorine-containing enynes. J. Fluorine Chem. 2001, 111, 81-90.
    • (2001) J. Fluorine Chem. , vol.111 , pp. 81-90
    • Ishizaki, M.1    Suzuki, D.2    Hoshino, O.3
  • 17
    • 77955184389 scopus 로고    scopus 로고
    • Rapid and slow generation of 1- trifluoromethylvinyllithium: Syntheses and applications of cf3-containing allylic alcohols, allylic amines, and vinyl ketones
    • Nadano, R.; Fuchibe, K.; Ikeda, M.; Takahashi, H.; Ichikawa, J. Rapid and Slow Generation of 1- Trifluoromethylvinyllithium: Syntheses and Applications of CF3-Containing Allylic Alcohols, Allylic Amines, and Vinyl Ketones. Chem. Asian J. 2010, 5, 1875-1883.
    • (2010) Chem. Asian J. , vol.5 , pp. 1875-1883
    • Nadano, R.1    Fuchibe, K.2    Ikeda, M.3    Takahashi, H.4    Ichikawa, J.5
  • 18
    • 34247272526 scopus 로고    scopus 로고
    • A facile synthesis of n-[2-(trifluoromethyl)allyl]amides and their transformation into angularly trifluoromethylated bicyclic cyclopentenones
    • Nadano, R.; Ichikawa, J. A facile synthesis of N-[2-(trifluoromethyl) allyl]amides and their transformation into angularly trifluoromethylated bicyclic cyclopentenones. Chem. Lett. 2007, 36, 22-23.
    • (2007) Chem. Lett. , vol.36 , pp. 22-23
    • Nadano, R.1    Ichikawa, J.2
  • 19
    • 84868533186 scopus 로고    scopus 로고
    • A novel synthesis of fluorine-containing cyclopentenones via pauson-khand reaction
    • Konno, T.; Kida, T.; Tani, A.; Ishihara, T. A novel synthesis of fluorine-containing cyclopentenones via Pauson-Khand reaction. J. Fluorine Chem. 2012, 144, 147-156.
    • (2012) J. Fluorine Chem. , vol.144 , pp. 147-156
    • Konno, T.1    Kida, T.2    Tani, A.3    Ishihara, T.4
  • 20
    • 84055190653 scopus 로고    scopus 로고
    • An improved copper-mediated oxidative trifluoromethylation of terminal alkynes
    • Zhang, K.; Qiu, X.; Huang, Y.; Qing, F. An Improved Copper-Mediated Oxidative Trifluoromethylation of Terminal Alkynes. Eur. J. Org. Chem. 2012, 58-61.
    • (2012) Eur. J. Org. Chem. , pp. 58-61
    • Zhang, K.1    Qiu, X.2    Huang, Y.3    Qing, F.4
  • 21
    • 77952859294 scopus 로고    scopus 로고
    • Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with me3sicf3
    • Chu, L.; Qing, F. Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3. J. Am. Chem. Soc. 2010, 132, 7262-7263.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 7262-7263
    • Chu, L.1    Qing, F.2
  • 22
    • 84863631947 scopus 로고    scopus 로고
    • Tetramethylnorbornadiene a versatile alkene for cyclopentenone synthesis through intermolecular pauson-khand reactions
    • Revés, M.; Lledö, A.; Ji, Y.; Blasi, E.; Riera, A.; Verdaguer, X. Tetramethylnorbornadiene, a versatile alkene for cyclopentenone synthesis through intermolecular Pauson-Khand reactions. Org. Lett. 2012, 14, 3534-3537.
    • (2012) Org. Lett. , vol.14 , pp. 3534-3537
    • Revés, M.1    Lledö, A.2    Ji, Y.3    Blasi, E.4    Riera, A.5    Verdaguer, X.6
  • 23
    • 84875773246 scopus 로고    scopus 로고
    • The pauson-khand reaction of medium sized trans-cycloalkenes
    • Lledö, A.; Fuster, A.; Revés, M.; Verdaguer, X.; Riera, A. The Pauson-Khand reaction of medium sized trans-cycloalkenes. Chem. Commun. 2013, 49, 3055-3057.
    • (2013) Chem. Commun. , vol.49 , pp. 3055-3057
    • Lledö, A.1    Fuster, A.2    Revés, M.3    Verdaguer, X.4    Riera, A.5
  • 24
    • 0034595752 scopus 로고    scopus 로고
    • Synthesis of tricyclic aromatic compounds by the intramolecular pauson-khand reaction promoted by molecular sieves
    • Perez-Serrano, L.; Blanco-Urgoiti, J.; Casarrubios, L.; Dominguez, G.; Perez-Castells, J. Synthesis of Tricyclic Aromatic Compounds by the Intramolecular Pauson-Khand Reaction Promoted by Molecular Sieves. J. Org. Chem. 2000, 65, 3513-3519.
    • (2000) J. Org. Chem. , vol.65 , pp. 3513-3519
    • Perez-Serrano, L.1    Blanco-Urgoiti, J.2    Casarrubios, L.3    Dominguez, G.4    Perez-Castells, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.