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Volumn 25, Issue 6, 2013, Pages 365-368

Optical purifications via self-disproportionation of enantiomers by achiral chromatography: Case study of a series of α-CF3-containing secondary alcohols

Author keywords

chiral recognition; chromatography; enantiomeric purification; fluorine and compounds

Indexed keywords

ALCOHOL DERIVATIVE;

EID: 84878388766     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22180     Document Type: Article
Times cited : (94)

References (57)
  • 1
    • 84891580093 scopus 로고    scopus 로고
    • Third Edition. New York: John Wiley and Sons
    • Ojima I, (Ed). Catalytic Asymmetric Synthesis, Third Edition. New York: John Wiley and Sons; 2010.
    • (2010) Catalytic Asymmetric Synthesis
    • Ojima, I.1
  • 2
    • 78149232497 scopus 로고    scopus 로고
    • On the Practical Limits of Determining Isolated Product Yields and Ratios of Stereoisomers: Reflections, Analysis, and Redemption
    • Wernerova M, Hudlicky T,. On the Practical Limits of Determining Isolated Product Yields and Ratios of Stereoisomers: Reflections, Analysis, and Redemption. Synlett 2010; 2701-2707.
    • (2010) Synlett , pp. 2701-2707
    • Wernerova, M.1    Hudlicky, T.2
  • 3
    • 77956648742 scopus 로고    scopus 로고
    • Rational application of self-disproportionation of enantiomers via sublimation - A novel methodological dimension for enantiomeric purifications
    • Ueki H, Yasumoto M, Soloshonok VA,. Rational application of self-disproportionation of enantiomers via sublimation-a novel methodological dimension for enantiomeric purifications. Tetrahedron-Asymmetry 2010; 21: 1396-1400.
    • (2010) Tetrahedron-Asymmetry , vol.21 , pp. 1396-1400
    • Ueki, H.1    Yasumoto, M.2    Soloshonok, V.A.3
  • 4
    • 79952740440 scopus 로고    scopus 로고
    • Self-Disproportionation of Enantiomers via Sublimation; New and Truly Green Dimension in Optical Purification
    • Han J, Nelson DJ, Sorochinsky AE, Soloshonok VA,. Self-Disproportionation of Enantiomers via Sublimation; New and Truly Green Dimension in Optical Purification. Curr Org Synth 2011; 8: 310-317.
    • (2011) Curr Org Synth , vol.8 , pp. 310-317
    • Han, J.1    Nelson, D.J.2    Sorochinsky, A.E.3    Soloshonok, V.A.4
  • 5
    • 84861125198 scopus 로고    scopus 로고
    • Self-Disproportionation of Enantiomers via Achiral Chromatography: A Warning and Extra Dimension in Optical Purifications
    • Soloshonok VA, Roussel C, Kitagawa O, Sorochinsky AE,. Self-Disproportionation of Enantiomers via Achiral Chromatography: a Warning and Extra Dimension in Optical Purifications. Chem Soc Rev 2012; 41: 4180-4188.
    • (2012) Chem Soc Rev , vol.41 , pp. 4180-4188
    • Soloshonok, V.A.1    Roussel, C.2    Kitagawa, O.3    Sorochinsky, A.E.4
  • 6
    • 84872189387 scopus 로고    scopus 로고
    • Self-Disproportionation of Enantiomers of Chiral, Non-Racemic Fluoroorganic Compounds: Role of Fluorine as Enabling Element
    • Sorochinsky AE, Aceña JL, Soloshonok VA,. Self-Disproportionation of Enantiomers of Chiral, Non-Racemic Fluoroorganic Compounds: Role of Fluorine as Enabling Element. Synthesis 2013; 45: 141-152.
    • (2013) Synthesis , vol.45 , pp. 141-152
    • Sorochinsky, A.E.1    Aceña, J.L.2    Soloshonok, V.A.3
  • 7
    • 33846839754 scopus 로고    scopus 로고
    • Self-Disproportionation of enantiomers on achiral phase chromatography. One more example of fluorine's magic powers
    • Soloshonok VA, Berbasov DO,. Self-Disproportionation of enantiomers on achiral phase chromatography. One more example of fluorine's magic powers. Chim Oggi/Chem Today 2006; 24: 44-47.
    • (2006) Chim Oggi/Chem Today , vol.24 , pp. 44-47
    • Soloshonok, V.A.1    Berbasov, D.O.2
  • 9
    • 33847330197 scopus 로고    scopus 로고
    • Serine sublimes with spontaneous chiral amplification
    • Perry RH, Wu C, Nefliu M, Cooks RG,. Serine sublimes with spontaneous chiral amplification. Chem Commun 2007; 1071-1073.
    • (2007) Chem Commun , pp. 1071-1073
    • Perry, R.H.1    Wu, C.2    Nefliu, M.3    Cooks, R.G.4
  • 10
    • 34250766709 scopus 로고    scopus 로고
    • An astrophysically-relevant mechanism for amino acid enantiomer enrichment
    • Fletcher SP, Jagt RBC, Feringa BL,. An astrophysically-relevant mechanism for amino acid enantiomer enrichment. Chem Commun 2007; 2578-2580.
    • (2007) Chem Commun , pp. 2578-2580
    • Fletcher, S.P.1    Jagt, R.B.C.2    Feringa, B.L.3
  • 11
    • 76949102871 scopus 로고    scopus 로고
    • A simple explanation of the enhancement or depletion of the enantiomeric excess in the partial sublimation of enantiomerically enriched amino acids
    • Bellec A, Guillemin JC,. A simple explanation of the enhancement or depletion of the enantiomeric excess in the partial sublimation of enantiomerically enriched amino acids. Chem Commun 2010; 46: 1482-1484.
    • (2010) Chem Commun , vol.46 , pp. 1482-1484
    • Bellec, A.1    Guillemin, J.C.2
  • 12
    • 77949488644 scopus 로고    scopus 로고
    • Attempts to explain the self-disproportionation observed in the partial sublimation of enantiomerically enriched carboxylic acids
    • Bellec A, Guillemin JC,. Attempts to explain the self-disproportionation observed in the partial sublimation of enantiomerically enriched carboxylic acids. J Fluorine Chem 2010; 131: 545-548.
    • (2010) J Fluorine Chem , vol.131 , pp. 545-548
    • Bellec, A.1    Guillemin, J.C.2
  • 14
    • 74449090371 scopus 로고    scopus 로고
    • Self-disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation
    • Yasumoto M, Ueki H, Soloshonok VA,. Self-disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation. J Fluorine Chem 2010; 131: 266-269.
    • (2010) J Fluorine Chem , vol.131 , pp. 266-269
    • Yasumoto, M.1    Ueki, H.2    Soloshonok, V.A.3
  • 15
    • 77949485705 scopus 로고    scopus 로고
    • Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation
    • Yasumoto M, Ueki H, Soloshonok VA,. Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation. J Fluorine Chem 2010; 131: 540-544.
    • (2010) J Fluorine Chem , vol.131 , pp. 540-544
    • Yasumoto, M.1    Ueki, H.2    Soloshonok, V.A.3
  • 16
    • 77949492088 scopus 로고    scopus 로고
    • Self-Disproportionation of Enantiomers via Sublimation: Isopropyl 3,3,3- (Trifluoro)Lactate
    • Yasumoto M, Ueki H, Ono T, Katagiri T, Soloshonok VA,. Self-Disproportionation of Enantiomers via Sublimation: Isopropyl 3,3,3- (Trifluoro)Lactate. J Fluorine Chem 2010; 131: 535-539.
    • (2010) J Fluorine Chem , vol.131 , pp. 535-539
    • Yasumoto, M.1    Ueki, H.2    Ono, T.3    Katagiri, T.4    Soloshonok, V.A.5
  • 17
    • 78651404643 scopus 로고    scopus 로고
    • Asymmetric amplification in amino acid sublimation involving racemic compound to conglomerate conversion
    • Viedma C, Noorduin WL, Ortiz JE, De Torres T, Cintas P,. Asymmetric amplification in amino acid sublimation involving racemic compound to conglomerate conversion. Chem Commun 2011; 47: 671-673.
    • (2011) Chem Commun , vol.47 , pp. 671-673
    • Viedma, C.1    Noorduin, W.L.2    Ortiz, J.E.3    De Torres, T.4    Cintas, P.5
  • 18
    • 0030558966 scopus 로고    scopus 로고
    • Separation of an enantiomorph and its racemate by distillation: Strong chiral recognizing ability of trifluorolactates
    • Katagiri T, Yoda C, Furuhashi K, Ueki K, Kubota T,. Separation of an enantiomorph and its racemate by distillation: strong chiral recognizing ability of trifluorolactates. Chem Lett 1996; 115-116.
    • (1996) Chem Lett , pp. 115-116
    • Katagiri, T.1    Yoda, C.2    Furuhashi, K.3    Ueki, K.4    Kubota, T.5
  • 19
    • 0035528549 scopus 로고    scopus 로고
    • Chiral Recognition by Multicenter Single Proton Hydrogen Bonding of Trifluorolactates
    • Katagiri T, Uneyama U,. Chiral Recognition by Multicenter Single Proton Hydrogen Bonding of Trifluorolactates. Chem Lett 2001; 1330-1331.
    • (2001) Chem Lett , pp. 1330-1331
    • Katagiri, T.1    Uneyama, U.2
  • 20
    • 77949490374 scopus 로고    scopus 로고
    • Discrimination of enantiomeric excess of optically active trifluorolactate by distillation: Evidence for a multi-center hydrogen bonding network in the liquid state
    • Katagiri T, Takahashi S, Tsuboi A, Suzaki M, Uneyama K,. Discrimination of enantiomeric excess of optically active trifluorolactate by distillation: Evidence for a multi-center hydrogen bonding network in the liquid state. J Fluorine Chem 2010; 131: 517-520.
    • (2010) J Fluorine Chem , vol.131 , pp. 517-520
    • Katagiri, T.1    Takahashi, S.2    Tsuboi, A.3    Suzaki, M.4    Uneyama, K.5
  • 21
    • 31444451709 scopus 로고    scopus 로고
    • Remarkable Amplification of the Self-Disproportionation of Enantiomers on Achiral-Phase Chromatography Columns
    • Soloshonok VA,. Remarkable Amplification of the Self-Disproportionation of Enantiomers on Achiral-Phase Chromatography Columns. Angew Chem Int Ed 2006; 45: 766-769.
    • (2006) Angew Chem Int Ed , vol.45 , pp. 766-769
    • Soloshonok, V.A.1
  • 22
    • 33745192709 scopus 로고    scopus 로고
    • BerbasovDO. Self-disproportionation of enantiomers of (R)-ethyl 3-(3,5-dinitrobenzamido)-4,4,4-trifluorobutanoate on achiral silica gel stationary phase
    • Soloshonok VA, BerbasovDO. Self-disproportionation of enantiomers of (R)-ethyl 3-(3,5-dinitrobenzamido)-4,4,4-trifluorobutanoate on achiral silica gel stationary phase. J Fluorine Chem 2006; 127: 597-603.
    • (2006) J Fluorine Chem , vol.127 , pp. 597-603
    • Soloshonok, V.A.1
  • 23
    • 77949492087 scopus 로고    scopus 로고
    • Self-disproportionation of enantiomers of heterocyclic compounds having a tertiary trifluoromethyl alcohol center on chromatography with a non-chiral system
    • Ogawa S, Nishimine T, Tokunaga E, Nakamura S, Shibata N,. Self-disproportionation of enantiomers of heterocyclic compounds having a tertiary trifluoromethyl alcohol center on chromatography with a non-chiral system. J Fluorine Chem 2010; 131: 521-524.
    • (2010) J Fluorine Chem , vol.131 , pp. 521-524
    • Ogawa, S.1    Nishimine, T.2    Tokunaga, E.3    Nakamura, S.4    Shibata, N.5
  • 24
    • 70549089933 scopus 로고    scopus 로고
    • Atropisomeric lactam chemistry: Catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors
    • Takahashi M, Tanabe H, Nakamura T, Kuribara H, Yamazaki T, Kitagawa O,. Atropisomeric lactam chemistry: catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors. Tetrahedron 2010; 66: 288-296.
    • (2010) Tetrahedron , vol.66 , pp. 288-296
    • Takahashi, M.1    Tanabe, H.2    Nakamura, T.3    Kuribara, H.4    Yamazaki, T.5    Kitagawa, O.6
  • 26
    • 0021076049 scopus 로고
    • 13C-labeled nicotine: Separation of enantiomers in a totally achiral system
    • 13C-labeled nicotine: separation of enantiomers in a totally achiral system. J Chromatogr 1983; 281: 17-33.
    • (1983) J Chromatogr , vol.281 , pp. 17-33
    • Cundy, K.C.1    Crooks, P.A.2
  • 27
    • 0032538773 scopus 로고    scopus 로고
    • Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation
    • Girard C, Kagan HB,. Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation. Angew Chem Int Ed 1998; 37: 2922-2959.
    • (1998) Angew Chem Int Ed , vol.37 , pp. 2922-2959
    • Girard, C.1    Kagan, H.B.2
  • 28
    • 0033849333 scopus 로고    scopus 로고
    • On diastereomeric perturbations
    • Girard C, Kagan HB,. On diastereomeric perturbations. Can J Chem 2000; 78: 816-828.
    • (2000) Can J Chem , vol.78 , pp. 816-828
    • Girard, C.1    Kagan, H.B.2
  • 29
    • 0001464746 scopus 로고
    • Self-amplification of optical activity by chromatography on an achiral adsorbent
    • Charles R, Gil-Av E,. Self-amplification of optical activity by chromatography on an achiral adsorbent. J Chromatogr 1984; 298: 516-520.
    • (1984) J Chromatogr , vol.298 , pp. 516-520
    • Charles, R.1    Gil-Av, E.2
  • 30
    • 0028331508 scopus 로고
    • Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation
    • Gil-Av E, Schurig V,. Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation. J Chromatogr A 1994; 666: 519-525.
    • (1994) J Chromatogr A , vol.666 , pp. 519-525
    • Gil-Av, E.1    Schurig, V.2
  • 31
    • 77956649479 scopus 로고    scopus 로고
    • Nonlinear effects in enantioselective chromatography: Prediction of unusual elution profiles of enantiomers in non-racemic mixtures on an achiral stationary phase doped with small amounts of a chiral selector
    • Trapp O, Schurig V,. Nonlinear effects in enantioselective chromatography: prediction of unusual elution profiles of enantiomers in non-racemic mixtures on an achiral stationary phase doped with small amounts of a chiral selector. Tetrahedron-Asymmetry 2010; 21: 1334-1340.
    • (2010) Tetrahedron-Asymmetry , vol.21 , pp. 1334-1340
    • Trapp, O.1    Schurig, V.2
  • 32
    • 0034965838 scopus 로고    scopus 로고
    • Simultaneous microbatch screening of enantiorecognition on solid chiral selectors using selected mixtures of test-racemates: A case study on cellulose tris(α-phenylpropionate) with configurational diversity
    • Roussel C, Bonnet B, De Riggi I, Suteu C,. Simultaneous microbatch screening of enantiorecognition on solid chiral selectors using selected mixtures of test-racemates: a case study on cellulose tris(α- phenylpropionate) with configurational diversity. Biomed Chromatogr 2001; 15: 173-180.
    • (2001) Biomed Chromatogr , vol.15 , pp. 173-180
    • Roussel, C.1    Bonnet, B.2    De Riggi, I.3    Suteu, C.4
  • 33
    • 23744440755 scopus 로고    scopus 로고
    • Enantiorecognition on solid chiral selectors using microbatch technology: An example of limitation in case of strong association in the racemate
    • Roussel C, Rafii E, Del Rio A, Vanthuyne N,. Enantiorecognition on solid chiral selectors using microbatch technology: an example of limitation in case of strong association in the racemate. Biomed Chromatogr 2005; 19: 434-438.
    • (2005) Biomed Chromatogr , vol.19 , pp. 434-438
    • Roussel, C.1    Rafii, E.2    Del Rio, A.3    Vanthuyne, N.4
  • 34
    • 58849105873 scopus 로고    scopus 로고
    • NMR and molecular modeling of the dimeric self-association of the enantiomers of 1,1′-bi-2-naphthol and 1-phenyl-2,2,2-trifluoroethanol in the solution state and their relevance to enantiomer self-disproportionation on achiral-phase chromatography (ESDAC)
    • Nieminen V, Murzin DY, Klika KD,. NMR and molecular modeling of the dimeric self-association of the enantiomers of 1,1′-bi-2-naphthol and 1-phenyl-2,2,2-trifluoroethanol in the solution state and their relevance to enantiomer self-disproportionation on achiral-phase chromatography (ESDAC). Org Biomol Chem 2009; 7: 537-542.
    • (2009) Org Biomol Chem , vol.7 , pp. 537-542
    • Nieminen, V.1    Murzin, D.Y.2    Klika, K.D.3
  • 35
    • 77949492203 scopus 로고    scopus 로고
    • NMR spectral enantioresolution of spirobrassinin and 1- methoxyspirobrassinin enantiomers using (S)-(-)-ethyl lactate and modeling of spirobrassinin self-association for rationalization of its self-induced diastereomeric anisochromism (SIDA) and enantiomer self-disproportionation on achiral-phase chromatography (ESDAC) phenomena
    • Klika KD, Budovska M, Kutschy P,. NMR spectral enantioresolution of spirobrassinin and 1-methoxyspirobrassinin enantiomers using (S)-(-)-ethyl lactate and modeling of spirobrassinin self-association for rationalization of its self-induced diastereomeric anisochromism (SIDA) and enantiomer self-disproportionation on achiral-phase chromatography (ESDAC) phenomena. J Fluorine Chem 2010; 131: 467-476.
    • (2010) J Fluorine Chem , vol.131 , pp. 467-476
    • Klika, K.D.1    Budovska, M.2    Kutschy, P.3
  • 37
    • 0030592749 scopus 로고    scopus 로고
    • The effect of substituents on the feasibility of azomethine-azomethine isomerization: New synthetic opportunities for biomimetic transamination
    • Soloshonok VA, Ono T,. The effect of substituents on the feasibility of azomethine-azomethine isomerization: New synthetic opportunities for biomimetic transamination. Tetrahedron 1996; 52: 14701-14712.
    • (1996) Tetrahedron , vol.52 , pp. 14701-14712
    • Soloshonok, V.A.1    Ono, T.2
  • 39
    • 0028329208 scopus 로고
    • Gold(I)-Catalyzed asymmetric aldol reaction of methyl isocyanoacetate with fluorinated benzaldehydes
    • Soloshonok VA, Hayashi T,. Gold(I)-Catalyzed asymmetric aldol reaction of methyl isocyanoacetate with fluorinated benzaldehydes. Tetrahedron Lett 1994; 35: 2713-2716.
    • (1994) Tetrahedron Lett , vol.35 , pp. 2713-2716
    • Soloshonok, V.A.1    Hayashi, T.2
  • 40
    • 0028307422 scopus 로고
    • Gold(I)-catalyzed asymmetric aldol reaction of fluorinated benzaldehydes with α-isocyanoacetamide
    • Soloshonok VA, Hayashi T,. Gold(I)-catalyzed asymmetric aldol reaction of fluorinated benzaldehydes with α-isocyanoacetamide. Tetrahedron-Asymmetry 1994; 5: 1091-1094.
    • (1994) Tetrahedron-Asymmetry , vol.5 , pp. 1091-1094
    • Soloshonok, V.A.1    Hayashi, T.2
  • 41
    • 0028258252 scopus 로고
    • Highly diastereoselective aldol reaction of fluoroalkyl aryl ketones with methyl isocyanoacetate catalyzed by silver(I)/triethylamine
    • Soloshonok VA, Hayashi T, Ishikawa K, Nagashima N,. Highly diastereoselective aldol reaction of fluoroalkyl aryl ketones with methyl isocyanoacetate catalyzed by silver(I)/triethylamine. Tetrahedron Lett 1994; 35: 1055-1058.
    • (1994) Tetrahedron Lett , vol.35 , pp. 1055-1058
    • Soloshonok, V.A.1    Hayashi, T.2    Ishikawa, K.3    Nagashima, N.4
  • 42
    • 84990137332 scopus 로고
    • Chromatographic Separation of the Excess Enantiomer under Achiral Conditions
    • Matusch R, Coors C,. Chromatographic Separation of the Excess Enantiomer under Achiral Conditions. Angew Chem Int Ed 1989; 28: 626-627.
    • (1989) Angew Chem Int Ed , vol.28 , pp. 626-627
    • Matusch, R.1    Coors, C.2
  • 44
    • 0033214139 scopus 로고    scopus 로고
    • General syntheses of optically active α-trifluoromethylated amines via ring-opening reactions of N-benzyl-2-trifluoromethylaziridine
    • Katagiri T, Takahashi M, Fujiwara Y, Ihara H, Uneyama K,. General syntheses of optically active α-trifluoromethylated amines via ring-opening reactions of N-benzyl-2-trifluoromethylaziridine. J Org Chem 1999; 64: 7323-7329.
    • (1999) J Org Chem , vol.64 , pp. 7323-7329
    • Katagiri, T.1    Takahashi, M.2    Fujiwara, Y.3    Ihara, H.4    Uneyama, K.5
  • 45
    • 0001939466 scopus 로고
    • Chiral Synthesis via Organoboranes. 40. Selective Reductions. 55. A Simple One-Pot Synthesis of the Enantiomers of Trifluoromethyloxirane. A General Synthesis in High Optical Purities of.alpha.-Trifluoromethyl Secondary Alcohols via the Ring-Cleavage Reactions of the Epoxide
    • Ramachandran PV, Gong B, Brown HC,. Chiral Synthesis via Organoboranes. 40. Selective Reductions. 55. A Simple One-Pot Synthesis of the Enantiomers of Trifluoromethyloxirane. A General Synthesis in High Optical Purities of.alpha.-Trifluoromethyl Secondary Alcohols via the Ring-Cleavage Reactions of the Epoxide. J Org Chem 1995; 60: 41-46.
    • (1995) J Org Chem , vol.60 , pp. 41-46
    • Ramachandran, P.V.1    Gong, B.2    Brown, H.C.3
  • 47
    • 0028328977 scopus 로고
    • Enantiomeric Enrichment of Sulfoxides by Preparative Flash Chromatography on an Achiral Phase
    • Diter P, Taudien S, Samuel O, Kagan HB,. Enantiomeric Enrichment of Sulfoxides by Preparative Flash Chromatography on an Achiral Phase. J Org Chem 1994; 59: 370-373.
    • (1994) J Org Chem , vol.59 , pp. 370-373
    • Diter, P.1    Taudien, S.2    Samuel, O.3    Kagan, H.B.4
  • 48
    • 23044459168 scopus 로고    scopus 로고
    • Intermolecular-medium and intramolecular-weak hydrogen bonding chains in the crystals of chiral trifluoromethylated amino alcohols
    • Katagiri T, Fujiwara Y, Takahashi S, Uneyama K,. Intermolecular-medium and intramolecular-weak hydrogen bonding chains in the crystals of chiral trifluoromethylated amino alcohols. J. Fluorine Chem 2005; 126: 1134-1139.
    • (2005) J. Fluorine Chem , vol.126 , pp. 1134-1139
    • Katagiri, T.1    Fujiwara, Y.2    Takahashi, S.3    Uneyama, K.4
  • 49
    • 0035929793 scopus 로고    scopus 로고
    • Diastereoselectivity controlled by electrostatic repulsion between the negative charge on a trifluoromethyl group and that on aromatic rings
    • Katagiri T, Yamaji S, Handa M, Irie M, Uneyama K,. Diastereoselectivity controlled by electrostatic repulsion between the negative charge on a trifluoromethyl group and that on aromatic rings. Chem Commun 2001; 2054-2055.
    • (2001) Chem Commun , pp. 2054-2055
    • Katagiri, T.1    Yamaji, S.2    Handa, M.3    Irie, M.4    Uneyama, K.5
  • 51
    • 0028237842 scopus 로고
    • Catalytic asymmetric synthesis of β-fluoroalkyl-β-amino acids via biomimetic [1,3]-proton shift reaction
    • Soloshonok VA, Kirilenko AG, Galushko SV, Kukhar VP,. Catalytic asymmetric synthesis of β-fluoroalkyl-β-amino acids via biomimetic [1,3]-proton shift reaction. Tetrahedron Lett 1994; 35: 5063-5064.
    • (1994) Tetrahedron Lett , vol.35 , pp. 5063-5064
    • Soloshonok, V.A.1    Kirilenko, A.G.2    Galushko, S.V.3    Kukhar, V.P.4
  • 53
    • 0029883406 scopus 로고    scopus 로고
    • Highly Diastereoselective Asymmetric Aldol Reactions of Chiral Ni(II)-Complex of Glycine with Trifluoromethyl Ketones
    • Soloshonok VA, Avilov DA, Kukhar VP,. Highly Diastereoselective Asymmetric Aldol Reactions of Chiral Ni(II)-Complex of Glycine with Trifluoromethyl Ketones. Tetrahedron-Asymmetry 1996; 7: 1547-1550.
    • (1996) Tetrahedron-Asymmetry , vol.7 , pp. 1547-1550
    • Soloshonok, V.A.1    Avilov, D.A.2    Kukhar, V.P.3
  • 54
    • 0030961675 scopus 로고    scopus 로고
    • Highly Diastereoselective aza-Aldol Reactions of a Chiral Ni(II) Complex of Glycine with Imines. An Efficient Asymmetric Approach to 3-Perfluoroalkyl-2, 3-Diamino Acids
    • Soloshonok VA, Avilov DA, Kukhar VP, Van Meervelt L, Mischenko N,. Highly Diastereoselective aza-Aldol Reactions of a Chiral Ni(II) Complex of Glycine with Imines. An Efficient Asymmetric Approach to 3-Perfluoroalkyl-2,3-Diamino Acids. Tetrahedron Lett 1997; 38: 4671-4674.
    • (1997) Tetrahedron Lett , vol.38 , pp. 4671-4674
    • Soloshonok, V.A.1    Avilov, D.A.2    Kukhar, V.P.3    Van Meervelt, L.4    Mischenko, N.5
  • 55
    • 0037416951 scopus 로고    scopus 로고
    • Chemo- and regioselectivity in the reactions between highly electrophilic fluorine containing dicarbonyl compounds and amines. Improved synthesis of the corresponding imines/enamines
    • Ohkura H, Berbasov DO, Soloshonok VA,. Chemo- and regioselectivity in the reactions between highly electrophilic fluorine containing dicarbonyl compounds and amines. Improved synthesis of the corresponding imines/enamines. Tetrahedron 2003; 59: 1647-1656.
    • (2003) Tetrahedron , vol.59 , pp. 1647-1656
    • Ohkura, H.1    Berbasov, D.O.2    Soloshonok, V.A.3
  • 56
    • 0030590464 scopus 로고    scopus 로고
    • Asymmetric Aldol Reactions of Trifluoromethyl Ketones with a Chiral Ni(II) Complex of Glycine: Stereocontrolling Effect of the Trifluoromethyl Group
    • Soloshonok VA, Avilov DV, Kukhar VP,. Asymmetric Aldol Reactions of Trifluoromethyl Ketones with a Chiral Ni(II) Complex of Glycine: Stereocontrolling Effect of the Trifluoromethyl Group. Tetrahedron 1996; 52: 12433-12442.
    • (1996) Tetrahedron , vol.52 , pp. 12433-12442
    • Soloshonok, V.A.1    Avilov, D.V.2    Kukhar, V.P.3
  • 57
    • 84870873368 scopus 로고    scopus 로고
    • Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate and their unusual crystallographic structure: The ultimate preference for homochiral intermolecular interactions
    • Aceña JL, Sorochinsky AE, Katagiri T, Soloshonok VA,. Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2- hydroxypropanoate and their unusual crystallographic structure: the ultimate preference for homochiral intermolecular interactions. Chem Commun 2013; 49: 373-375.
    • (2013) Chem Commun , vol.49 , pp. 373-375
    • Aceña, J.L.1    Sorochinsky, A.E.2    Katagiri, T.3    Soloshonok, V.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.