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Volumn 21, Issue 1, 2009, Pages 24-34

A rational approach to predict and modulate stereolability of chiral α substituted ketones

Author keywords

Asymmetric synthesis; Chemical design; Enantiomerization; Enolization; Keto enol tautomerism; MAO inhibitors; Molecular modeling; Racemization

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING); KETONE; PROTON; WATER; ACETONITRILE; ACETONITRILE DERIVATIVE; CARBON; HYDROGEN; MONOAMINE OXIDASE INHIBITOR; PYRROLIDINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 59849121710     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20589     Document Type: Article
Times cited : (15)

References (40)
  • 1
    • 0344609024 scopus 로고    scopus 로고
    • α-epimerizable nonracemic ketones and aldehydes can be accessed by crystallization-induced dynamic resolution of imines
    • Kosmrlj J, Weigel LO, Evans DA, Downey CW, Wu J. Unfunctionalized, α-epimerizable nonracemic ketones and aldehydes can be accessed by crystallization-induced dynamic resolution of imines. J Am Chem Soc 2003;125:3208-3209.
    • (2003) J Am Chem Soc , vol.125 , pp. 3208-3209
    • Kosmrlj, J.1    Weigel, L.O.2    Evans, D.A.3    Downey, C.W.4    Wu, J.5    Unfunctionalized6
  • 2
    • 0028319079 scopus 로고
    • Base-catalyzed racemization of 3-O-acyloxazepam
    • Yang SK, Bao Z. Base-catalyzed racemization of 3-O-acyloxazepam. Chirality 1994;6:321.
    • (1994) Chirality , vol.6 , pp. 321
    • Yang, S.K.1    Bao, Z.2
  • 3
    • 2442489096 scopus 로고    scopus 로고
    • Rapid racemization in thiazolidinediones: A quantum chemical study
    • Bharatam PV, Khanna S. Rapid racemization in thiazolidinediones: a quantum chemical study. J Phys Chem 2004;108:3784-3788.
    • (2004) J Phys Chem , vol.108 , pp. 3784-3788
    • Bharatam, P.V.1    Khanna, S.2
  • 4
    • 0028784530 scopus 로고
    • Low configurational stability of amfepramone and cathinone: Mechanism and kinetics of chiral inversion
    • Reist M, Christiansen LH, Christoffersen P, Carrupt PA, Testa B. Low configurational stability of amfepramone and cathinone: mechanism and kinetics of chiral inversion. Chirality 1995;7:469-473.
    • (1995) Chirality , vol.7 , pp. 469-473
    • Reist, M.1    Christiansen, L.H.2    Christoffersen, P.3    Carrupt, P.A.4    Testa, B.5
  • 5
    • 0028220747 scopus 로고
    • Investigations on the in vitro racemization of thalidomide by high-performance liquid chromatography
    • Knoche B, Blaschke G. Investigations on the in vitro racemization of thalidomide by high-performance liquid chromatography. J Chromatogr A 1994;666:235-240.
    • (1994) J Chromatogr A , vol.666 , pp. 235-240
    • Knoche, B.1    Blaschke, G.2
  • 6
    • 0026437190 scopus 로고    scopus 로고
    • Annoncement. FDA's policy statement for the development of new stereoisomeric drugs. Chirality 1992;4:338.
    • Annoncement. FDA's policy statement for the development of new stereoisomeric drugs. Chirality 1992;4:338.
  • 7
    • 21844464544 scopus 로고    scopus 로고
    • Contributions to the theory and practice of the chromatographic separation of enantiomers
    • Schurig V. Contributions to the theory and practice of the chromatographic separation of enantiomers. Chirality 2005;17:S205-S226.
    • (2005) Chirality , vol.17
    • Schurig, V.1
  • 11
    • 0031000294 scopus 로고    scopus 로고
    • Enantiomerization barriers by dynamic HPLC. Stationary phase effects
    • Gasparrini F, Misiti D, Pierini M, Villani C. Enantiomerization barriers by dynamic HPLC. Stationary phase effects. Tetrahedron Asymmetry 1997;8:2069-2073.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 2069-2073
    • Gasparrini, F.1    Misiti, D.2    Pierini, M.3    Villani, C.4
  • 12
    • 0034679101 scopus 로고    scopus 로고
    • Comparison of dynamic HPLC and dynamic NMR in the study of conformational stereodynamics: Case of the enantiomers of a hindered secondary phosphine oxide
    • Gasparrini F, Lunazzi L, Mazzanti A, Pierini M, Pieyrusiewicz KM, Villani C. Comparison of dynamic HPLC and dynamic NMR in the study of conformational stereodynamics: case of the enantiomers of a hindered secondary phosphine oxide. J Am Chem Soc 2000;122:4776-4780.
    • (2000) J Am Chem Soc , vol.122 , pp. 4776-4780
    • Gasparrini, F.1    Lunazzi, L.2    Mazzanti, A.3    Pierini, M.4    Pieyrusiewicz, K.M.5    Villani, C.6
  • 13
    • 0035686746 scopus 로고    scopus 로고
    • Chromatographic resolution and enantionerization barriers of axially chiral 1-naphthamides
    • Gasparrini F, D'acquarica I, Pierini M, Villani C. Chromatographic resolution and enantionerization barriers of axially chiral 1-naphthamides. J Sep Sci 2001;24:941-946.
    • (2001) J Sep Sci , vol.24 , pp. 941-946
    • Gasparrini, F.1    D'acquarica, I.2    Pierini, M.3    Villani, C.4
  • 14
    • 22244434936 scopus 로고    scopus 로고
    • Stereolabile chiral compounds: Analysis by dynamic chromatography and stopped-flow methods
    • Wolf C. Stereolabile chiral compounds: analysis by dynamic chromatography and stopped-flow methods. Chem Soc Rev 2005;34:595-608.
    • (2005) Chem Soc Rev , vol.34 , pp. 595-608
    • Wolf, C.1
  • 15
    • 0037040637 scopus 로고    scopus 로고
    • Conformational studies by dynamic NMR. 86. Structure, stereodynamics, and cryogenic enantioseparation of the stereolabile isomers of o-dinaphthylphenyl derivatives
    • Dell'Erba C, Gasparrini F, Grilli S, Lunazzi L, Mazzanti A, Novi M, Pierini M, Tafani C, Villani C. Conformational studies by dynamic NMR. 86. Structure, stereodynamics, and cryogenic enantioseparation of the stereolabile isomers of o-dinaphthylphenyl derivatives. J Org Chem 2002;67:1663-1668.
    • (2002) J Org Chem , vol.67 , pp. 1663-1668
    • Dell'Erba, C.1    Gasparrini, F.2    Grilli, S.3    Lunazzi, L.4    Mazzanti, A.5    Novi, M.6    Pierini, M.7    Tafani, C.8    Villani, C.9
  • 16
    • 0030744067 scopus 로고    scopus 로고
    • Determination of the enantiomerization barrier of arylnaphthalene lignans by cryogenic subcritical fluid chromatography and computer simulation
    • Wolf C, Pirkle WH, Welch CJ, Hochmuth DH, König WA, Chee G-L, Charlton JL. Determination of the enantiomerization barrier of arylnaphthalene lignans by cryogenic subcritical fluid chromatography and computer simulation. J Org Chem 1997;62:5208-5210.
    • (1997) J Org Chem , vol.62 , pp. 5208-5210
    • Wolf, C.1    Pirkle, W.H.2    Welch, C.J.3    Hochmuth, D.H.4    König, W.A.5    Chee, G.-L.6    Charlton, J.L.7
  • 17
    • 0037462372 scopus 로고    scopus 로고
    • Stable simple enols. Resolution of chiral 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylethenol. A different racemization mechanism for the enol and its acetate
    • Rochlin E, Rappoport Z. Stable simple enols. Resolution of chiral 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylethenol. A different racemization mechanism for the enol and its acetate. J Org Chem 2003;68:216-226.
    • (2003) J Org Chem , vol.68 , pp. 216-226
    • Rochlin, E.1    Rappoport, Z.2
  • 18
    • 0037012931 scopus 로고    scopus 로고
    • Conformational studies by dynamic NMR. 89. Stereomutation and cryogenic enantioseparation of conformational antipodes of hindered aryl oximes
    • Gasparrini F, Grilli S, Leardini R, Lunazzi L, Mazzanti A, Nanni D, Pierini M, Pinamonti M. Conformational studies by dynamic NMR. 89. Stereomutation and cryogenic enantioseparation of conformational antipodes of hindered aryl oximes. J Org Chem 2002;67:3089-3095.
    • (2002) J Org Chem , vol.67 , pp. 3089-3095
    • Gasparrini, F.1    Grilli, S.2    Leardini, R.3    Lunazzi, L.4    Mazzanti, A.5    Nanni, D.6    Pierini, M.7    Pinamonti, M.8
  • 19
  • 20
    • 20844448412 scopus 로고    scopus 로고
    • Stereolabile and configurationally stable atropisomers of hindered aryl carbinols
    • Casarini D, Coluccini C, Lunazzi L, Mazzanti A. Stereolabile and configurationally stable atropisomers of hindered aryl carbinols. J Org Chem 2005;70:5098-5102.
    • (2005) J Org Chem , vol.70 , pp. 5098-5102
    • Casarini, D.1    Coluccini, C.2    Lunazzi, L.3    Mazzanti, A.4
  • 21
    • 0037424483 scopus 로고    scopus 로고
    • Conformational studies by dynamic NMR. 93. Stereomutation, enantioseparation, and absolute configuration of the atropisomers of diarylbicyclononanes
    • Casarini D, Rosini C, Grilli S, Lunazzi L, Mazzanti A. Conformational studies by dynamic NMR. 93. Stereomutation, enantioseparation, and absolute configuration of the atropisomers of diarylbicyclononanes. J Org Chem 2003;68:1815-1820.
    • (2003) J Org Chem , vol.68 , pp. 1815-1820
    • Casarini, D.1    Rosini, C.2    Grilli, S.3    Lunazzi, L.4    Mazzanti, A.5
  • 23
    • 0028040396 scopus 로고
    • Enantiomerization of 2,2′-diisopropylbiphenyl during chiral inclusion gas chromatography: Determination of the rotational energy barrier by computer simulation of dynamic chromatographic elution profiles
    • Jung H, Fluck M, Schurig V. Enantiomerization of 2,2′-diisopropylbiphenyl during chiral inclusion gas chromatography: determination of the rotational energy barrier by computer simulation of dynamic chromatographic elution profiles. Chirality 1994;6:510-512.
    • (1994) Chirality , vol.6 , pp. 510-512
    • Jung, H.1    Fluck, M.2    Schurig, V.3
  • 24
    • 0029873490 scopus 로고    scopus 로고
    • Determination of enantiomerization barriers by computer simulation of experimental elution profiles obtained by high-performance liquid chromatography on a chiral stationary phase
    • Cabrera K, Jung M, Fluck M, Schurig V. Determination of enantiomerization barriers by computer simulation of experimental elution profiles obtained by high-performance liquid chromatography on a chiral stationary phase. J ChromatogrA 1996;731:315-321.
    • (1996) J ChromatogrA , vol.731 , pp. 315-321
    • Cabrera, K.1    Jung, M.2    Fluck, M.3    Schurig, V.4
  • 25
    • 0033543476 scopus 로고    scopus 로고
    • Galli B, Gasparrini F, Lanzotti V, Misiti D, Riccio R, Villani C, Guan-Fu H, Zhong-Wu M, Wan-Fe Y. Grandione, a new heptacyclic dimeric diterpene from Torreya grandis Fort. Tetrahedron 1999;55:11385-11394.
    • Galli B, Gasparrini F, Lanzotti V, Misiti D, Riccio R, Villani C, Guan-Fu H, Zhong-Wu M, Wan-Fe Y. Grandione, a new heptacyclic dimeric diterpene from Torreya grandis Fort. Tetrahedron 1999;55:11385-11394.
  • 26
    • 0037080475 scopus 로고    scopus 로고
    • Stereointegrity of thalidomide: Gaschromatographic determination of the enantiomerization barrier
    • Trapp O, Schoetz G, Schurig V. Stereointegrity of thalidomide: gaschromatographic determination of the enantiomerization barrier. J Pharm Biomed Anal 2002;27:497-505.
    • (2002) J Pharm Biomed Anal , vol.27 , pp. 497-505
    • Trapp, O.1    Schoetz, G.2    Schurig, V.3
  • 27
    • 0037453639 scopus 로고    scopus 로고
    • Enantiomerization study of some α-nitroketones by dynamic high-resolution gas chromatography
    • Gasparrini F, Pierini M, Villani C, De Maria P, Fontana A, Ballini R. Enantiomerization study of some α-nitroketones by dynamic high-resolution gas chromatography. J Org Chem 2003;68:3173-3177.
    • (2003) J Org Chem , vol.68 , pp. 3173-3177
    • Gasparrini, F.1    Pierini, M.2    Villani, C.3    De Maria, P.4    Fontana, A.5    Ballini, R.6
  • 28
    • 35648952796 scopus 로고    scopus 로고
    • High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability
    • Cirilli R, Ferretti R, La Torre F, Secci D, Bolasco A, Carradori S, Pierini M. High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability. J Chromatogr A 2007;1172:160-169.
    • (2007) J Chromatogr A , vol.1172 , pp. 160-169
    • Cirilli, R.1    Ferretti, R.2    La Torre, F.3    Secci, D.4    Bolasco, A.5    Carradori, S.6    Pierini, M.7
  • 29
    • 0001483754 scopus 로고    scopus 로고
    • Predicting the rates of proton transfer reactions: A simple model using equilibrium constants and distortion energies
    • Guthrie JP. Predicting the rates of proton transfer reactions: a simple model using equilibrium constants and distortion energies. J Phys Org Chem 1998;11:632-641.
    • (1998) J Phys Org Chem , vol.11 , pp. 632-641
    • Guthrie, J.P.1
  • 31
    • 0004258726 scopus 로고
    • 2nd ed, chapter 10. Cornell University Press, Ithaca, New York
    • Bell RP. The proton in chemistry, 2nd ed., chapter 10. Cornell University Press, Ithaca, New York, 1973.
    • (1973) The proton in chemistry
    • Bell, R.P.1
  • 32
    • 0030567338 scopus 로고    scopus 로고
    • a of ethyl acetate: Bronsted correlation for deprotonation of a simple oxygen ester in aqueous solution
    • a of ethyl acetate: bronsted correlation for deprotonation of a simple oxygen ester in aqueous solution. J Am Chem Soc 1996;118:3129-3141.
    • (1996) J Am Chem Soc , vol.118 , pp. 3129-3141
    • Amyes, T.L.1    Richard, J.P.2
  • 33
    • 34249818809 scopus 로고    scopus 로고
    • Ionization and tautomerization of 2-nitrocyclohexanone in aqueous solution
    • Angelini G, De Maria P, Fontana A, Pierini M, Siani G. Ionization and tautomerization of 2-nitrocyclohexanone in aqueous solution. J Org Chem 2007;72:4039-4047.
    • (2007) J Org Chem , vol.72 , pp. 4039-4047
    • Angelini, G.1    De Maria, P.2    Fontana, A.3    Pierini, M.4    Siani, G.5
  • 34
    • 0000972439 scopus 로고
    • Kinetics of the dehydration of methylene glycol in aqueous solution
    • Bell RP, Evans PG. Kinetics of the dehydration of methylene glycol in aqueous solution. Proc R Soc Lond Ser A 1966;291:297-323.
    • (1966) Proc R Soc Lond Ser A , vol.291 , pp. 297-323
    • Bell, R.P.1    Evans, P.G.2
  • 36
    • 33744915257 scopus 로고    scopus 로고
    • The 2-oxocyclobutanecarboxylic acid keto-enol system in aqueous solution: A remarkable acid-strengthening effect of the cyclobutane ring
    • Chang JA, Chiang Y, Keeffe JR, Kresge AJ, Nikolaev VA, Popik VV. The 2-oxocyclobutanecarboxylic acid keto-enol system in aqueous solution: a remarkable acid-strengthening effect of the cyclobutane ring. J Org Chem 2006;71:4460-4467.
    • (2006) J Org Chem , vol.71 , pp. 4460-4467
    • Chang, J.A.1    Chiang, Y.2    Keeffe, J.R.3    Kresge, A.J.4    Nikolaev, V.A.5    Popik, V.V.6
  • 37
    • 37049068467 scopus 로고
    • Equilibrium constants for ionisation and enolisation of 2-phenylacetylfuran
    • Fontana A, More O'Ferrall RA. Equilibrium constants for ionisation and enolisation of 2-phenylacetylfuran. J Chem Soc, Perkin Trans. 1994;2:2453-2459.
    • (1994) J Chem Soc, Perkin Trans , vol.2 , pp. 2453-2459
    • Fontana, A.1    More O'Ferrall, R.A.2
  • 38
    • 0037453478 scopus 로고    scopus 로고
    • Enantioselective liquid chromatography of C3-chiral 2,3-dihydro-1,2,5-benzothiadiazepin-4(5H)-one and thione 1,1-dioxides on polyacrylamide- and polysaccharide-based chiral stationary phases
    • Cirilli R, Costi R, Di Santo R, Artico M, Roux A, Gallinella B, Zanitti L, La Torre F. Enantioselective liquid chromatography of C3-chiral 2,3-dihydro-1,2,5-benzothiadiazepin-4(5H)-one and thione 1,1-dioxides on polyacrylamide- and polysaccharide-based chiral stationary phases. J Chromatogr A. 2003;993:17-28.
    • (2003) J Chromatogr A , vol.993 , pp. 17-28
    • Cirilli, R.1    Costi, R.2    Di Santo, R.3    Artico, M.4    Roux, A.5    Gallinella, B.6    Zanitti, L.7    La Torre, F.8
  • 39
    • 0037016285 scopus 로고    scopus 로고
    • Analytical and semipreparative enantiomeric separation of azole antifungal agents by high-performance liquid chromatography on polysaccharide-based chiral stationary phases: Application to in vitro biological studies
    • Cirilli R, Costi R, Di Santo R, Ferretti R, La Torre F, Angiolella L, Micocci M. Analytical and semipreparative enantiomeric separation of azole antifungal agents by high-performance liquid chromatography on polysaccharide-based chiral stationary phases: application to in vitro biological studies. J Chromatogr A 2002;942:107-114.
    • (2002) J Chromatogr A , vol.942 , pp. 107-114
    • Cirilli, R.1    Costi, R.2    Di Santo, R.3    Ferretti, R.4    La Torre, F.5    Angiolella, L.6    Micocci, M.7


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