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Volumn 22, Issue 6, 2010, Pages 548-556

Molecular tweezers for enantiodiscrimination in NMR: Di-(R,R)-1-[10-(1- hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2, 2-trifluoroethyl benzenedicarboxylates

Author keywords

Chiral solvating agents; Enantiodiscrimination; Enantiomeric excess; Molecular tweezers; NMR

Indexed keywords

DI 1 [10 (1 HYDROXY 2,2,2 TRIFLUOROETHYL) 9 ANTHRYL] 2,2,2 TRIFLUOROETHYLISOPHTHALIC ACID; DI 1 [10 (1 HYDROXY 2,2,2 TRIFLUOROETHYL) 9 ANTHRYL] 2,2,2 TRIFLUOROETHYLPHTHALIC ACID; DI 1 [10 (1 HYDROXY 2,2,2 TRIFLUOROETHYL) 9 ANTHRYL] 2,2,2 TRIFLUOROETHYLTEREPHTHALIC ACID; DICARBOXYLIC ACID; PHTHALIC ACID; UNCLASSIFIED DRUG;

EID: 77951554643     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20786     Document Type: Article
Times cited : (9)

References (29)
  • 1
    • 33645038629 scopus 로고    scopus 로고
    • Do the Terms "% ee" and "% de" make sense as expressions of stereoisomer composition or stereoselectivity?
    • Gawlay RE. Do the Terms "% ee" and "% de" make sense as expressions of stereoisomer composition or stereoselectivity? J Org Chem 2006;71:2411-2416.
    • (2006) J Org Chem , vol.71 , pp. 2411-2416
    • Gawlay, R.E.1
  • 2
    • 0037287499 scopus 로고    scopus 로고
    • Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy
    • Wenzel TJ, Wilcox JD. Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy. Chirality 2003;15:256-270.
    • (2003) Chirality , vol.15 , pp. 256-270
    • Wenzel, T.J.1    Wilcox, J.D.2
  • 3
    • 0000237404 scopus 로고
    • NMR determination of enantiomeric purity
    • Parker D. NMR determination of enantiomeric purity. Chem Rev 1991;91:1441-1457.
    • (1991) Chem Rev , vol.91 , pp. 1441-1457
    • Parker, D.1
  • 4
    • 0942277395 scopus 로고    scopus 로고
    • The assignment of absolute configuration by NMR
    • Seco JM, Quiñoá E, Riguera R. The assignment of absolute configuration by NMR. Chem Rev 2004;104:17-117.
    • (2004) Chem Rev , vol.104 , pp. 17-117
    • Seco, J.M.1    Quiñoá, E.2    Riguera, R.3
  • 7
    • 0034897924 scopus 로고    scopus 로고
    • Chiral recognition of dipeptide methyl esters by an anionic beta-cyclodextrin
    • DOI 10.1002/chir.1064
    • Kano K, Hasegawa H, Miyamura M. Chiral recognition of dipeptide methyl esters by an anionic beta-cyclodextrin. Chirality 2001;13:474-482. (Pubitemid 32729805)
    • (2001) Chirality , vol.13 , Issue.8 , pp. 474-482
    • Kano, K.1    Hasegawa, H.2    Miyamura, M.3
  • 8
    • 0033098235 scopus 로고    scopus 로고
    • Chiral recognition of phenylacetic acid derivatives by aminated cyclodextrins
    • Kitae T, Takashima H, Kano K. Chiral recognition of phenylacetic acid derivatives by aminated cyclodextrins. J Inclusion Phenom 1999;33:345-359.
    • (1999) J Inclusion Phenom , vol.33 , pp. 345-359
    • Kitae, T.1    Takashima, H.2    Kano, K.3
  • 9
    • 0034741420 scopus 로고    scopus 로고
    • Chiral recognition of (18-crown-6)-tetracarboxylic acid as a chiral selector determined by NMR spectroscopy
    • Bang H, Edwards JO, Kim J, Lawler RG, Reynolds K, Ryan WJ, Sweigart DA. Chiral recognition of (18-crown-6)-tetracarboxylic acid as a chiral selector determined by NMR spectroscopy. J Chem Soc Perkin Trans 2001;2:1685-1692. (Pubitemid 33332110)
    • (2001) Journal of the Chemical Society, Perkin Transactions 2 , Issue.9 , pp. 1685-1692
    • Bang, E.1    Jung, J.-W.2    Lee, W.3    Lee, D.W.4    Lee, W.5
  • 10
    • 0035926483 scopus 로고    scopus 로고
    • Utility of crown ethers derived from methyl b-image-galactopyranoside and their lanthanide couples as chiral NMR discriminating agents
    • Wenzel TJ, Thurston JE, Sek DC, Joly JP. Utility of crown ethers derived from methyl b-image-galactopyranoside and their lanthanide couples as chiral NMR discriminating agents. Tetrahedron: Asymmetry 2001;12:1125-1130.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1125-1130
    • Wenzel, T.J.1    Thurston, J.E.2    Sek, D.C.3    Joly, J.P.4
  • 11
    • 9444250434 scopus 로고    scopus 로고
    • Chiral molecular tweezers
    • Harmata M. Chiral molecular tweezers. Acc Chem Res 2004;37:862-873.
    • (2004) Acc Chem Res , vol.37 , pp. 862-873
    • Harmata, M.1
  • 13
    • 0034680655 scopus 로고    scopus 로고
    • Bile acid-derived molecular tweezers: Study of solvent effects in binding, and determination of thermodynamic parameters by an extraction-based protocol
    • Potluri VK, Maitra U. Bile acid-derived molecular tweezers: study of solvent effects in binding, and determination of thermodynamic parameters by an extraction-based protocol. J Org Chem 2000;65:7764-7769.
    • (2000) J Org Chem , vol.65 , pp. 7764-7769
    • Potluri, V.K.1    Maitra, U.2
  • 14
    • 0027986545 scopus 로고
    • Molecular clefts. 4. An approach to structural analogs of echinomycin: Synthesis of a new class of synthetic molecular tweezers
    • Harmata M, Barnes CL, Srinivasa RK, Elahmad S. Molecular clefts. 4. An approach to structural analogs of echinomycin: synthesis of a new class of synthetic molecular tweezers. J Am Chem Soc 1994;116:8392-8393.
    • (1994) J Am Chem Soc , Issue.116 , pp. 8392-8393
    • Harmata, M.1    Barnes, C.L.2    Srinivasa, R.K.3    Elahmad, S.4
  • 16
    • 0026659841 scopus 로고
    • Optically active trans-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3- dioxacyclopentane and its derivatives as chiral shift reagents for the determination of enantiomeric purity and absolute configuration
    • Tanaka K, Ootani M, Toda F. Optically active trans- bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane and its derivatives as chiral shift reagents for the determination of enantiomeric purity and absolute configuration. Tetrahedron: Asymmetry 1992;3:709-712.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 709-712
    • Tanaka, K.1    Ootani, M.2    Toda, F.3
  • 17
    • 33750010592 scopus 로고    scopus 로고
    • Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2, 2-trifluoroethyl muconate: A highly chiral cavity for enantiodiscrimination by NMR
    • Palomino-Schätzlein M, Virgili A, Gil S, Jaime C. Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl muconate: a highly chiral cavity for enantiodiscrimination by NMR. J Org Chem 2006;71:8114-8120.
    • (2006) J Org Chem , vol.71 , pp. 8114-8120
    • Palomino-Schätzlein, M.1    Virgili, A.2    Gil, S.3    Jaime, C.4
  • 18
    • 0037039931 scopus 로고    scopus 로고
    • Preparation and structural study of the enantiomers of α,α′-bis(trifluoromethyl)-9,10-anthracenedimethanol and its perdeuterated isotopomer, highly effective chiral solvating agents
    • DOI 10.1021/jo015957e
    • Pomares M, Sánchez-Ferrando F, Virgili A, Alvarez-Larena A, Piniella JF. Preparation and structural study of the enantiomers of α,α′-bis(tri-fluoromethyl)-9,10-anthracenedimethanol and its perdeuterated Isotopomer, highly effective chiral solvating agents. J Org Chem 2002; 67:753-758. (Pubitemid 34135675)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.3 , pp. 753-758
    • Pomares, M.1    Sanchez-Ferrando, F.2    Virgili, A.3    Alvarez-Larena, A.4    Piniella, J.F.5
  • 19
    • 2142770240 scopus 로고    scopus 로고
    • α,α′-Bis(trifluoromethyl)-9,10-anthracenedimethanol: Enantioselective synthesis and bidentate complexes with benzenedimethanols
    • DOI 10.1016/j.tetasy.2004.03.019, PII S0957416604001971
    • Estivill C, Ivanov PM, Pomares M, Sánchez-Arís M, Virgili A. α,α′-Bis(trifluoromethyl)-9,10-anthracenedimethanol: enantioselective synthesis and bidentate complexes with benzenedimethanols. Tetrahedron: Asymmetry 2004;15:1431-1436. (Pubitemid 38553770)
    • (2004) Tetrahedron Asymmetry , vol.15 , Issue.9 , pp. 1431-1436
    • Estivill, C.1    Ivanov, P.M.2    Pomares, M.3    Sanchez-Aris, M.4    Virgili, A.5
  • 20
    • 84856265285 scopus 로고    scopus 로고
    • version 9.0. New Cork, NY: Schrödinger, LLC
    • MacroModel, version 9.0. New Cork, NY: Schrödinger, LLC; 2005.
    • (2005) MacroModel
  • 23
    • 0043162336 scopus 로고
    • An internal-coordinate Monte Carlo method for searching conformational space
    • Chang G, Guida WC, Still WC. An internal-coordinate Monte Carlo method for searching conformational space. J Am Chem Soc 1989; 111:4379-4386.
    • (1989) J Am Chem Soc , vol.111 , pp. 4379-4386
    • Chang, G.1    Guida, W.C.2    Still, W.C.3
  • 24
    • 0007793280 scopus 로고
    • Conformations of cycloheptadecane. a comparison of methods for conformational searching
    • Chang G, Guida WC, Still WC. Conformations of cycloheptadecane. A comparison of methods for conformational searching. J Am Chem Soc 1990;112:1419-1427.
    • (1990) J Am Chem Soc , vol.112 , pp. 1419-1427
    • Chang, G.1    Guida, W.C.2    Still, W.C.3
  • 26
    • 0001308921 scopus 로고
    • A rapid approximation to the solvent accessible surface areas of atoms
    • Hasel W, Hendrickson TF, Still WC. A rapid approximation to the solvent accessible surface areas of atoms. Tetrahedron Comput Methodol 1988;1:103-116.
    • (1988) Tetrahedron Comput Methodol , vol.1 , pp. 103-116
    • Hasel, W.1    Hendrickson, T.F.2    Still, W.C.3
  • 27
    • 0344778061 scopus 로고
    • Semianalytical treatment of solvation for molecular mechanics and dynamics
    • Still WC, Tempczyck A, Hawley C, Hendrickson T. Semianalytical treatment of solvation for molecular mechanics and dynamics. J Am Chem Soc 1990;112:6127-6129.
    • (1990) J Am Chem Soc , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyck, A.2    Hawley, C.3    Hendrickson, T.4
  • 28
    • 0031553175 scopus 로고    scopus 로고
    • GB/SA-based continuum solvation model for octanol
    • Best SA, Merz KM, Reynolds CH. GB/SA-based continuum solvation model for octanol. J Phys Chem B 1997;101:10479-10487.
    • (1997) J Phys Chem B , vol.101 , pp. 10479-10487
    • Best, S.A.1    Merz, K.M.2    Reynolds, C.H.3
  • 29
    • 0024821263 scopus 로고
    • Molecular mechanics. The MM3 force field for hydrocarbons
    • Allinger NL, Yuh IH, Lii JH. Molecular mechanics. The MM3 force field for hydrocarbons. J Am Chem Soc 1989;111:8551-8770.
    • (1989) J Am Chem Soc , vol.111 , pp. 8551-8770
    • Allinger, N.L.1    Yuh, I.H.2    Lii, J.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.