메뉴 건너뛰기




Volumn 24, Issue 5, 2012, Pages 391-399

Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography

Author keywords

interaction; binaphthyl; chiral stationary phases; click chemistry; thermodynamic parameters

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 2,2' DIHYDROXY 1,1' BINAPHTHYL;

EID: 84860425797     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22039     Document Type: Article
Times cited : (7)

References (38)
  • 1
    • 0035847272 scopus 로고    scopus 로고
    • Separation of enantiomers: Needs, challenges, perspectives
    • Maier NM, Franco P, Lindner W,. Separation of enantiomers: needs, challenges, perspectives. J Chromatogr A 2001; 906: 3-33.
    • (2001) J Chromatogr A , vol.906 , pp. 3-33
    • Maier, N.M.1    Franco, P.2    Lindner, W.3
  • 2
    • 56549116899 scopus 로고    scopus 로고
    • Chiral HPLC for efficient resolution of enantiomers
    • Okamoto Y, Ikai T,. Chiral HPLC for efficient resolution of enantiomers. Chem Soc Rev 2008; 37: 2593-2608.
    • (2008) Chem Soc Rev , vol.37 , pp. 2593-2608
    • Okamoto, Y.1    Ikai, T.2
  • 3
    • 1342265558 scopus 로고    scopus 로고
    • Preparation and chiral recognition of a novel chiral stationary phase for high-performance liquid chromatography, based on mono(6(A)-N-allylamino-6(A)- deoxy)-perfunctionalized beta-cyclodextrin and covalently bonded silica gel
    • Lai XH, Ng SC,. Preparation and chiral recognition of a novel chiral stationary phase for high-performance liquid chromatography, based on mono(6(A)-N-allylamino-6(A)-deoxy)-perfunctionalized beta-cyclodextrin and covalently bonded silica gel. J Chromatogr A 2004; 1031: 135-142.
    • (2004) J Chromatogr A , vol.1031 , pp. 135-142
    • Lai, X.H.1    Ng, S.C.2
  • 4
    • 0001151298 scopus 로고
    • A widely useful chiral stationary phase for the high-performance liquid chromatography separation of enantiomers
    • Pirkle WH, Finn JM, Schreiner JL, Hamper BC,. A widely useful chiral stationary phase for the high-performance liquid chromatography separation of enantiomers. J Am Chem Soc 1981; 103: 3964-3966.
    • (1981) J Am Chem Soc , vol.103 , pp. 3964-3966
    • Pirkle, W.H.1    Finn, J.M.2    Schreiner, J.L.3    Hamper, B.C.4
  • 5
    • 0035847245 scopus 로고    scopus 로고
    • Protein-based chiral stationary phases for high-performance liquid chromatography enantioseparations
    • Haginaka J, Protein-based chiral stationary phases for high-performance liquid chromatography enantioseparations. J Chromatogr A 2001; 906: 253-273.
    • (2001) J Chromatogr A , vol.906 , pp. 253-273
    • Haginaka, J.1
  • 7
    • 0028227322 scopus 로고
    • Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography
    • Armstrong DW, Tang Y, Chen S, Zhou Y, Bagwill C, Chen J-R,. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Anal Chem 1994; 66: 1473-1484.
    • (1994) Anal Chem , vol.66 , pp. 1473-1484
    • Armstrong, D.W.1    Tang, Y.2    Chen, S.3    Zhou, Y.4    Bagwill, C.5    Chen, J.-R.6
  • 8
    • 21544462875 scopus 로고    scopus 로고
    • Influence of mobile phase composition on the apparent thermodynamic characteristics in liquid chromatographic enantioseparation on a tartardiamide-based stationary phase
    • DOI 10.1365/s10337-005-0560-5
    • Weng W, Zeng QL, Yao BX, Wang QH, Li SQ,. Influence of mobile phase composition on the apparent thermodynamic characteristics in liquid chromatographic enantioseparation on a tartardiamide-based stationary phase. Chromatographia 2005; 61: 561-566. (Pubitemid 40922138)
    • (2005) Chromatographia , vol.61 , Issue.11-12 , pp. 561-566
    • Weng, W.1    Zeng, Q.2    Yao, B.3    Wang, Q.4    Li, S.5
  • 9
    • 4444360295 scopus 로고    scopus 로고
    • Study of the mechanism of enantioseparation Part VI: Thermodynamic study of HPLC separation of some enantiomers of phenylcarbamic acid derivatives on a (S,S) Whelk-O 1 column
    • DOI 10.1002/jssc.200301591
    • Dungelova J, Lehotay J, Krupcik J, Cizmarik J, Armstrong DW,. Study of the mechanism of enantioseparation-part VI: thermodynamic study of HPLC separation of some enantiomers of phenylcarbamic acid derivatives on a (SS) Whelk-O 1 column. J Sep Sci 2004; 27: 983-990. (Pubitemid 39173339)
    • (2004) Journal of Separation Science , vol.27 , Issue.12 , pp. 983-990
    • Dungelova, J.1    Lehotay, J.2    Krupcik, J.3    Cizmarik, J.4    Armstrong, D.W.5
  • 10
    • 34247232580 scopus 로고    scopus 로고
    • The docking of chiral epoxides on the Whelk-O1 stationary phase: A molecular dynamics study
    • DOI 10.1016/j.chroma.2007.03.073, PII S0021967307004797
    • Zhao CF, Cann NM,. The docking of chiral epoxides on the Whelk-O1 stationary phase: a molecular dynamics study. J Chromatogr A 2007; 1149: 197-218. (Pubitemid 46627643)
    • (2007) Journal of Chromatography A , vol.1149 , Issue.2 , pp. 197-218
    • Zhao, C.1    Cann, N.M.2
  • 11
    • 17244369977 scopus 로고    scopus 로고
    • BINOL: A versatile chiral reagent
    • Brunel JM,. BINOL: a versatile chiral reagent. Chem Rev 2005; 105 (3): 857-898.
    • (2005) Chem Rev , vol.105 , Issue.3 , pp. 857-898
    • Brunel, J.M.1
  • 12
    • 0038245255 scopus 로고    scopus 로고
    • Ldquo catalyst analogue rdquo: A concept for constructing multicomponent asymmetric catalysts (MAC) by using a polymer support13
    • Takayoshi A, Tetuya S, Kazuhiro O, Shinobu T, Hiroaki S,. Ldquo catalyst analogue rdquo: a concept for constructing multicomponent asymmetric catalysts (MAC) by using a polymer support13. Angew Chem Int Ed 2003; 42: 2144-2147.
    • (2003) Angew Chem Int Ed , vol.42 , pp. 2144-2147
    • Takayoshi, A.1    Tetuya, S.2    Kazuhiro, O.3    Shinobu, T.4    Hiroaki, S.5
  • 13
    • 0038312014 scopus 로고    scopus 로고
    • Facile optical resolution of tert-butanethiosulfinate by molecular complexation with (R)-BINOL and study of chiral discrimination of the diastereomeric complexes
    • Jian L, Xiaoxia S, Xin C, Kaibei Y, Jin Z, Jingen D,. Facile optical resolution of tert-butanethiosulfinate by molecular complexation with (R)-BINOL and study of chiral discrimination of the diastereomeric complexes. Chem-Euro J 2003; 9: 2611-2615.
    • (2003) Chem - Euro J , vol.9 , pp. 2611-2615
    • Jian, L.1    Xiaoxia, S.2    Xin, C.3    Kaibei, Y.4    Jin, Z.5    Jingen, D.6
  • 14
    • 4344625966 scopus 로고    scopus 로고
    • Asymmetric allylboration of aldehydes and ketones using 3,3′-disubstitutedbinaphthol-modified boronates
    • DOI 10.1021/ol0490882
    • Wu TR, Shen LX, Chong JM,. Asymmetric allylboration of aldehydes and ketones using 3,3 '-disubstitutedbinaphthol-modified boronates. Org Lett 2004; 6: 2701-2704. (Pubitemid 39118975)
    • (2004) Organic Letters , vol.6 , Issue.16 , pp. 2701-2704
    • Wu, T.R.1    Shen, L.2    Chong, J.M.3
  • 15
    • 26444565729 scopus 로고    scopus 로고
    • Quinoid BINOL-type compounds as a novel class of chiral ligands
    • DOI 10.1016/j.tetasy.2005.08.026, PII S0957416605006385
    • Minatti A, Dotz KH,. Quinoid BINOL-type compounds as a novel class of chiral ligands. Tetrahedron: Asymmetry 2005; 16: 3256-3267. (Pubitemid 41427057)
    • (2005) Tetrahedron Asymmetry , vol.16 , Issue.19 , pp. 3256-3267
    • Minatti, A.1    Dotz, K.H.2
  • 16
    • 54249131552 scopus 로고    scopus 로고
    • Chromatographic enantioseparations of binaphthyl compounds on an immobilized polysaccharide-based chiral stationary phase
    • Weng W, Guo H, Zhan F, Fang H, Wang Q, Yao B, Li S,. Chromatographic enantioseparations of binaphthyl compounds on an immobilized polysaccharide-based chiral stationary phase. J Chromatogr A 2008; 1210: 178-184.
    • (2008) J Chromatogr A , vol.1210 , pp. 178-184
    • Weng, W.1    Guo, H.2    Zhan, F.3    Fang, H.4    Wang, Q.5    Yao, B.6    Li, S.7
  • 17
    • 38049083344 scopus 로고    scopus 로고
    • Enantioseparation of binaphthol and its derivatives on cellulose tris(3,5-dimethylphenyl carbamate)
    • Weng W, Zhan FP, Fu J, Li T, Chen XJ, Huang XJ,. Enantioseparation of binaphthol and its derivatives on cellulose tris(3,5-dimethylphenyl carbamate). Chromatographia 2008; 67: 119-123.
    • (2008) Chromatographia , vol.67 , pp. 119-123
    • Weng, W.1    Zhan, F.P.2    Fu, J.3    Li, T.4    Chen, X.J.5    Huang, X.J.6
  • 18
    • 77952151236 scopus 로고    scopus 로고
    • Comparison of HPLC enantioseparation of substituted binaphthyls on CD-, polysaccharide- and synthetic polymer-based chiral stationary phases
    • Loukotkova L, Tesarova E, Bosakova Z, Repko P, Armstrong DW,. Comparison of HPLC enantioseparation of substituted binaphthyls on CD-, polysaccharide- and synthetic polymer-based chiral stationary phases. J Sep Sci 2010; 33: 1244-1254.
    • (2010) J Sep Sci , vol.33 , pp. 1244-1254
    • Loukotkova, L.1    Tesarova, E.2    Bosakova, Z.3    Repko, P.4    Armstrong, D.W.5
  • 19
    • 30144433042 scopus 로고    scopus 로고
    • Highly efficient chromatographic resolution of α,α′- dihydroxybiaryls
    • DOI 10.1021/ol052309z
    • Huang J, Li T,. Highly Efficient Chromatographic Resolution of a,a'-Dihydroxybiaryls. Org Lett 2005; 7: 5821-5823. (Pubitemid 43052861)
    • (2005) Organic Letters , vol.7 , Issue.26 , pp. 5821-5823
    • Huang, J.1    Li, T.2
  • 20
    • 0029949417 scopus 로고    scopus 로고
    • NMR studies of chiral discrimination relevant to the liquid chromatographic enantioseparation by a cellulose phenylcarbamate derivative
    • DOI 10.1021/ja960050x
    • Yashima E, Yamamoto C, Okamoto Y,. NMR studies of chiral discrimination relevant to the liquid chromatographic enantioseparation by a cellulose phenylcarbamate derivative. J Am Chem Soc 1996; 118: 4036-4048. (Pubitemid 26175173)
    • (1996) Journal of the American Chemical Society , vol.118 , Issue.17 , pp. 4036-4048
    • Yashima, E.1    Yamamoto, C.2    Okamoto, Y.3
  • 21
    • 0035149115 scopus 로고    scopus 로고
    • Chiral recognition of binaphthyl derivatives: A chiral recognition model on the basis of chromatography, spectroscopy, and molecular mechanistic calculations for the enantioseparation of 1,1 '-binaphthyl derivatives on cholic acid-bonded stationary phases
    • Vaton-Chanvrier L, Oulyadi H, Combret Y, Coquerel G, Combret JC,. Chiral recognition of binaphthyl derivatives: a chiral recognition model on the basis of chromatography, spectroscopy, and molecular mechanistic calculations for the enantioseparation of 1,1 '-binaphthyl derivatives on cholic acid-bonded stationary phases. Chirality 2001; 13: 668-674.
    • (2001) Chirality , vol.13 , pp. 668-674
    • Vaton-Chanvrier, L.1    Oulyadi, H.2    Combret, Y.3    Coquerel, G.4    Combret, J.C.5
  • 22
    • 36949002870 scopus 로고
    • High-performance liquid chromatographic separation of enantiomers on axially chiral binaphthalene derivatives bonded to silica gel
    • Yamashita J, Numakura T, Kita H, Suzuki T, Oi S, Miyano S, Hashimoto H, Takai N,. High-performance liquid chromatographic separation of enantiomers on axially chiral binaphthalene derivatives bonded to silica gel. J Chromatogr A 1987; 403: 275-279.
    • (1987) J Chromatogr A , vol.403 , pp. 275-279
    • Yamashita, J.1    Numakura, T.2    Kita, H.3    Suzuki, T.4    Oi, S.5    Miyano, S.6    Hashimoto, H.7    Takai, N.8
  • 23
    • 0027218247 scopus 로고
    • Chiral stationary phases consisting of axially dissymetric 2'-substituted-1,1'-binaphthyl-2-carboxylic acids bonded to silica gel for high-performance liquid chromatographic separation of enantiomers
    • DOI 10.1016/0021-9673(93)80614-E
    • Oi S, Shijo M, Tanaka H, Miyano S, Yamashita J,. Chiral stationary phases consisting of axially dissymmetric 2'-substituted-1,1'-binaphthyl-2-carboxylic acids bonded to silica gel for high-performance liquid chromatographic separation of enantiomers. J Chromatogr A 1993; 645: 17-28. (Pubitemid 23245441)
    • (1993) Journal of Chromatography , vol.645 , Issue.1 , pp. 17-28
    • Oi, S.1    Shijo, M.2    Tanaka, H.3    Miyano, S.4    Yamashita, J.5
  • 24
    • 0028327145 scopus 로고
    • Investigation on the chiral discrimination mechanism using an axially asymmetric binaphthalene-based stationary phase for high- performance liquid chromatography
    • DOI 10.1016/0021-9673(94)85008-9
    • Oi S, Ono H, Tanaka H, Matsuzaka Y, Miyano S,. Investigation on the chiral discrimination mechanism using an axially asymmetric binaphthalene-based stationary phase for high-performance liquid chromatography. J Chromatogr A 1994; 659: 75-86. (Pubitemid 24096169)
    • (1994) Journal of Chromatography A , vol.659 , Issue.1 , pp. 75-86
    • Oi, S.1    Ono, H.2    Tanaka, H.3    Matsuzaka, Y.4    Miyano, S.5
  • 25
    • 79955695044 scopus 로고    scopus 로고
    • Preparation of "click" binaphthyl stationary phase and its application for separation of anthraquinones from Rheum palmatum L
    • Yu D, Yu H, Wang X, Jin Y, Ke Y, Liang X,. Preparation of "click" binaphthyl stationary phase and its application for separation of anthraquinones from Rheum palmatum L. J Sep Sci 2011; 34: 1133-1140.
    • (2011) J Sep Sci , vol.34 , pp. 1133-1140
    • Yu, D.1    Yu, H.2    Wang, X.3    Jin, Y.4    Ke, Y.5    Liang, X.6
  • 26
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • Kolb HC, Finn MG, Sharpless KB,. Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 2001; 40: 2004-2021.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 27
    • 80052795489 scopus 로고    scopus 로고
    • Novel Pirkle-type quinine 3,5-dinitrophenylcarbamate chiral stationary phase implementing click chemistry
    • Kacprzak KM, Lindner W,. Novel Pirkle-type quinine 3,5- dinitrophenylcarbamate chiral stationary phase implementing click chemistry. J Sep Sci 2011; 34: 2391-2396.
    • (2011) J Sep Sci , vol.34 , pp. 2391-2396
    • Kacprzak, K.M.1    Lindner, W.2
  • 28
    • 79951720434 scopus 로고    scopus 로고
    • Triazolo-linked cinchona alkaloid carbamate anion exchange-type chiral stationary phases: Synthesis by click chemistry and evaluation
    • Kacprzak KM, Maier NM, Lindner W,. Triazolo-linked cinchona alkaloid carbamate anion exchange-type chiral stationary phases: synthesis by click chemistry and evaluation. J Chromatogr A 2011; 1218: 1452-1460.
    • (2011) J Chromatogr A , vol.1218 , pp. 1452-1460
    • Kacprzak, K.M.1    Maier, N.M.2    Lindner, W.3
  • 29
    • 78449287869 scopus 로고    scopus 로고
    • "Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography
    • Wang Y, Young DJ, Tan TTY, Ng SC,. "Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography. J Chromatogr A 2010; 1217: 7878-7883.
    • (2010) J Chromatogr A , vol.1217 , pp. 7878-7883
    • Wang, Y.1    Young, D.J.2    Tan, T.T.Y.3    Ng, S.C.4
  • 30
    • 77956907286 scopus 로고    scopus 로고
    • Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase
    • Kacprzak KM, Maier NM, Lindner W,. Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase. J Sep Sci 2010; 33: 2590-2598.
    • (2010) J Sep Sci , vol.33 , pp. 2590-2598
    • Kacprzak, K.M.1    Maier, N.M.2    Lindner, W.3
  • 31
    • 61349125674 scopus 로고    scopus 로고
    • "Clickable" SBA-15 mesoporous materials: Synthesis, characterization and their reaction with alkynes
    • Malvi B, Sarkar BR, Pati D, Mathew R, Ajithkumar TG, Sen Gupta S,. "Clickable" SBA-15 mesoporous materials: synthesis, characterization and their reaction with alkynes. J Mater Chem 2009; 19: 1409-1416.
    • (2009) J Mater Chem , vol.19 , pp. 1409-1416
    • Malvi, B.1    Sarkar, B.R.2    Pati, D.3    Mathew, R.4    Ajithkumar, T.G.5    Sen Gupta, S.6
  • 32
    • 33748644066 scopus 로고    scopus 로고
    • Synthesis of 3,3'-, 6,6'- and 3,3',6,6'-substituted binaphthols and their application in the asymmetric hydrophosphonylation of aldehydes-an obvious effect of substituents of BINOL on the enantioselectivity
    • Qian CT, Huang TS, Zhu CJ, Sun J,. Synthesis of 3,3'-, 6,6'- and 3,3',6,6'-substituted binaphthols and their application in the asymmetric hydrophosphonylation of aldehydes-an obvious effect of substituents of BINOL on the enantioselectivity. J Chem Soc-Perkin Trans1 1998; 1998: 2097-2104.
    • (1998) J Chem Soc - Perkin Trans1 , vol.1998 , pp. 2097-2104
    • Qian, C.T.1    Huang, T.S.2    Zhu, C.J.3    Sun, J.4
  • 33
    • 0142026976 scopus 로고    scopus 로고
    • Study on the mechanism of chiral recognition with molecularly imprinted polymers
    • DOI 10.1016/S0003-2670(03)00708-6
    • Lu Y, Li CX, Zhang HS, Liu XH,. Study on the mechanism of chiral recognition with molecularly imprinted polymers. Anal Chim Acta 2003; 489: 33-43. (Pubitemid 37272010)
    • (2003) Analytica Chimica Acta , vol.489 , Issue.1 , pp. 33-43
    • Lu, Y.1    Li, C.2    Zhang, H.3    Liu, X.4
  • 34
    • 0032545240 scopus 로고    scopus 로고
    • Effect of temperature on retention of enantiomers of β-methyl amino acids on a teicoplanin chiral stationary phase
    • DOI 10.1016/S0021-9673(98)00835-8, PII S0021967398008358
    • Peter A, Torok G, Armstrong DW, Toth G, Tourwe D,. Effect of temperature on retention of enantiomers of beta-methyl amino acids on a teicoplanin chiral stationary phase. J Chromatogr A 1998; 828: 177-190. (Pubitemid 29046415)
    • (1998) Journal of Chromatography A , vol.828 , Issue.1-2 , pp. 177-190
    • Peter, A.1    Torok, G.2    Armstrong, D.W.3    Toth, G.4    Tourwe, D.5
  • 35
    • 0037035817 scopus 로고    scopus 로고
    • Effects of temperature on retention of chiral compounds on a ristocetin A chiral stationary phase
    • DOI 10.1016/S0021-9673(02)00390-4, PII S0021967302003904
    • Peter A, Vekes E, Armstrong DW,. Effects of temperature on retention of chiral compounds on a ristocetin A chiral stationary phase. J Chromatogr A 2002; 958: 89-107. (Pubitemid 34556942)
    • (2002) Journal of Chromatography A , vol.958 , Issue.1-2 , pp. 89-107
    • Peter, A.1    Vekes, E.2    Armstrong, D.W.3
  • 36
    • 9644265214 scopus 로고    scopus 로고
    • Temperature and enantioseparation by macrocyclic glycopeptide chiral stationary phases
    • DOI 10.1016/j.chroma.2004.05.072, PII S0021967304008507
    • Berthod A, He BLF, Beesley TE,. Temperature and enantioseparation by macrocyclic glycopeptide chiral stationary phases. J Chromatogr A 2004; 1060: 205-214. (Pubitemid 39573286)
    • (2004) Journal of Chromatography A , vol.1060 , Issue.1-2 SPEC.ISS. , pp. 205-214
    • Berthod, A.1    He, B.L.2    Beesley, T.E.3
  • 37
    • 3042565492 scopus 로고    scopus 로고
    • Enantioseparation of amino acid derivatives on an immobilized network polymer derived from L-tartaric acid
    • DOI 10.1016/j.chroma.2004.05.058, PII S0021967304008118
    • Weng W, Wang QH, Yao BX, Le Zeng Q,. Enantio separation of amino acid derivatives on an immobilized network polymer derived from l -tartaric acid. J Chromatogr A 2004; 1042: 81-87. (Pubitemid 38813355)
    • (2004) Journal of Chromatography A , vol.1042 , Issue.1-2 , pp. 81-87
    • Weng, W.1    Wang, Q.H.2    Yao, B.X.3    Zeng, Q.L.4
  • 38
    • 0028274617 scopus 로고
    • Enantiomeric separation of chiral sulphoxides. Screening of cellulose-based sorbents with particular reference to cellulose tribenzoate
    • DOI 10.1016/0021-9673(94)80401-X
    • Küsters E, Loux V, Schmid E, Floersheim P,. Enantiomeric separation of chiral sulphoxides: screening of cellulose-based sorbents with particular reference to cellulose tribenzoate. J Chromatogr A 1994; 666: 421-432. (Pubitemid 24138231)
    • (1994) Journal of Chromatography A , vol.666 , Issue.1-2 , pp. 421-432
    • Kusters, E.1    Loux, V.2    Schmid, E.3    Floersheim, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.