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Volumn 91, Issue 5, 2014, Pages 716-721

Undergraduate laboratory experiment to determine absolute configuration using thin-layer chromatography

Author keywords

Catalysis; Enantiomers; Hands On Learning Manipulatives; Kinetics; Laboratory Instruction; Organic Chemistry; Problem Solving Decision Making; Second Year Undergraduate; Stereochemistry; Thin Layer Chromatography

Indexed keywords


EID: 84900532076     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/ed4004996     Document Type: Article
Times cited : (13)

References (34)
  • 1
    • 31544472407 scopus 로고
    • Molecular structure and chirality
    • Brand, D. J.; Fisher, J. Molecular structure and chirality J. Chem. Educ. 1987, 64, 1035-1038
    • (1987) J. Chem. Educ. , vol.64 , pp. 1035-1038
    • Brand, D.J.1    Fisher, J.2
  • 2
    • 0035508202 scopus 로고    scopus 로고
    • Demonstrating chirality: Using a mirror with physical models to show non-superimposability of chiral molecules with their mirror images
    • Collins, M. J. Demonstrating chirality: Using a mirror with physical models to show non-superimposability of chiral molecules with their mirror images J. Chem. Educ. 2001, 78, 1484-1485
    • (2001) J. Chem. Educ. , vol.78 , pp. 1484-1485
    • Collins, M.J.1
  • 3
    • 78650141964 scopus 로고    scopus 로고
    • Using Molecular Representations to Aid Student Understanding of Stereochemical Concepts
    • Abraham, M.; Varghese, V.; Tang, H. Using Molecular Representations To Aid Student Understanding of Stereochemical Concepts J. Chem. Educ. 2010, 87, 1425-1429
    • (2010) J. Chem. Educ. , vol.87 , pp. 1425-1429
    • Abraham, M.1    Varghese, V.2    Tang, H.3
  • 4
    • 3242878147 scopus 로고    scopus 로고
    • Critical Thinking in the Chemistry Classroom and beyond
    • Jacob, C. Critical Thinking in the Chemistry Classroom and Beyond J. Chem. Educ. 2004, 81, 1216-1223
    • (2004) J. Chem. Educ. , vol.81 , pp. 1216-1223
    • Jacob, C.1
  • 5
    • 0035447612 scopus 로고    scopus 로고
    • Teaching Science Problem Solving: An Overview of Experimental Work
    • Lyle, K. S.; Robinson, W. R. Teaching Science Problem Solving: An Overview of Experimental Work J. Chem. Educ. 2001, 78, 1162-1163
    • (2001) J. Chem. Educ. , vol.78 , pp. 1162-1163
    • Lyle, K.S.1    Robinson, W.R.2
  • 7
    • 0942277395 scopus 로고    scopus 로고
    • The Assignment of Absolute Configuration by NMR
    • Seco, J. M.; Quiñoá, E.; Riguera, R. The Assignment of Absolute Configuration by NMR Chem. Rev. 2004, 104, 17-118
    • (2004) Chem. Rev. , vol.104 , pp. 17-118
    • Seco, J.M.1    Quiñoá, E.2    Riguera, R.3
  • 8
    • 79951503684 scopus 로고    scopus 로고
    • Assignment of absolute configuration using chiral reagents and NMR spectroscopy
    • Wenzel, T. J.; Chisholm, C. D. Assignment of absolute configuration using chiral reagents and NMR spectroscopy Chirality 2011, 23, 190-214
    • (2011) Chirality , vol.23 , pp. 190-214
    • Wenzel, T.J.1    Chisholm, C.D.2
  • 10
    • 0010640653 scopus 로고
    • α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
    • Dale, J. A.; Dull, D. L.; Mosher, H. S. α-Methoxy-α- trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines J. Org. Chem. 1969, 34, 2543-2549
    • (1969) J. Org. Chem. , vol.34 , pp. 2543-2549
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 11
    • 2142858450 scopus 로고
    • High-field FT NMR application of Moshers method. the absolute configurations of marine terpenoids
    • Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. High-field FT NMR application of Moshers method. The absolute configurations of marine terpenoids J. Am. Chem. Soc. 1991, 113, 4092-4096
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092-4096
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 12
    • 38449102399 scopus 로고    scopus 로고
    • Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons
    • For a review of the advanced Mosher method procedure, see: Hoye, T. R.; Jeffrey, C. S.; Shao, F. Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons Nat. Protoc. 2007, 2, 2451-2458
    • (2007) Nat. Protoc. , vol.2 , pp. 2451-2458
    • Hoye, T.R.1    Jeffrey, C.S.2    Shao, F.3
  • 13
    • 0242322522 scopus 로고    scopus 로고
    • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism
    • For a review on using vibrational circular dichroism, see - 758
    • For a review on using vibrational circular dichroism, see: Freedman, T. B.; Cao, X.; Dukor, R. K.; Nafie, L. A. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism Chirality 2003, 15, 743-758
    • (2003) Chirality , vol.15 , pp. 743
    • Freedman, T.B.1    Cao, X.2    Dukor, R.K.3    Nafie, L.A.4
  • 14
    • 84879625261 scopus 로고    scopus 로고
    • Electronic CD Exciton Chirality Method: Principles and Applications
    • For a review on the electronic CD exciton chirality method, see: In, Vol. Applications in Stereochemical Analysis of Synthetic Compounds, Natural Products, and Biomolecules; Berova, N. Polavarapu, P. L. Nakanishi, K. Woody, R. W. John Wiley & Sons, Inc. Hoboken, NJ - 166
    • For a review on the electronic CD exciton chirality method, see: Harada, N.; Nakanishi, K.; Berova, N. Electronic CD Exciton Chirality Method: Principles and Applications. In Comprehensive Chiroptical Spectroscopy, Vol. 2: Applications in Stereochemical Analysis of Synthetic Compounds, Natural Products, and Biomolecules; Berova, N..; Polavarapu, P. L.; Nakanishi, K..; Woody, R. W., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2012; pp 115-166.
    • (2012) Comprehensive Chiroptical Spectroscopy , vol.2 , pp. 115
    • Harada, N.1    Nakanishi, K.2    Berova, N.3
  • 15
    • 0037034361 scopus 로고    scopus 로고
    • Toward the Creation of NMR Databases in Chiral Solvents: Bidentate Chiral NMR Solvents for Assignment of the Absolute Configuration of Acyclic Secondary Alcohols
    • Kobayashi, Y.; Hayashi, N.; Kishi, Y. Toward the Creation of NMR Databases in Chiral Solvents: Bidentate Chiral NMR Solvents for Assignment of the Absolute Configuration of Acyclic Secondary Alcohols Org. Lett. 2002, 4, 411-414
    • (2002) Org. Lett. , vol.4 , pp. 411-414
    • Kobayashi, Y.1    Hayashi, N.2    Kishi, Y.3
  • 16
    • 0042335750 scopus 로고    scopus 로고
    • Application of chiral bidentate NMR solvents for assignment of the absolute configuration of alcohols: Scope and limitation
    • Kobayashi, Y.; Hayashi, N.; Kishi, Y. Application of chiral bidentate NMR solvents for assignment of the absolute configuration of alcohols: scope and limitation Tetrahedron Lett. 2003, 44, 7489-7491
    • (2003) Tetrahedron Lett. , vol.44 , pp. 7489-7491
    • Kobayashi, Y.1    Hayashi, N.2    Kishi, Y.3
  • 17
    • 11444259272 scopus 로고    scopus 로고
    • Applications of Chiral Lanthanide Shift Reagents for Assignment of Absolute Configuration of Alcohols
    • Ghosh, I.; Zeng, H.; Kishi, Y. Applications of Chiral Lanthanide Shift Reagents for Assignment of Absolute Configuration of Alcohols Org. Lett. 2004, 6, 4715-4718
    • (2004) Org. Lett. , vol.6 , pp. 4715-4718
    • Ghosh, I.1    Zeng, H.2    Kishi, Y.3
  • 18
    • 11444261456 scopus 로고    scopus 로고
    • Use of a Chiral Praseodymium Shift Reagent in Predicting the Complete Stereostructure of Glisoprenin A
    • Ghosh, I.; Kishi, Y.; Tomoda, H.; Omura, S. Use of a Chiral Praseodymium Shift Reagent in Predicting the Complete Stereostructure of Glisoprenin A Org. Lett. 2004, 6, 4719-4722
    • (2004) Org. Lett. , vol.6 , pp. 4719-4722
    • Ghosh, I.1    Kishi, Y.2    Tomoda, H.3    Omura, S.4
  • 19
    • 43249096494 scopus 로고    scopus 로고
    • Determination of absolute configuration of secondary alcohols using lipase-catalyzed kinetic resolutions
    • Jing, Q.; Kazlauskas, R. J. Determination of absolute configuration of secondary alcohols using lipase-catalyzed kinetic resolutions Chirality 2008, 20, 724-735
    • (2008) Chirality , vol.20 , pp. 724-735
    • Jing, Q.1    Kazlauskas, R.J.2
  • 20
    • 43249092579 scopus 로고    scopus 로고
    • The use of X-ray crystallography to determine absolute configuration
    • For a review on X-ray crystallographic analysis, see - 690
    • For a review on X-ray crystallographic analysis, see: Flack, H. D.; Bernardinelli, G. The use of X-ray crystallography to determine absolute configuration Chirality 2008, 20, 681-690
    • (2008) Chirality , vol.20 , pp. 681
    • Flack, H.D.1    Bernardinelli, G.2
  • 21
    • 43349101505 scopus 로고    scopus 로고
    • Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines
    • Allen, D. A.; Tomaso, A. E.; Priest, O. P.; Hindson, D. F.; Hurlburt, J. L. Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines J. Chem. Educ. 2008, 85, 698-700
    • (2008) J. Chem. Educ. , vol.85 , pp. 698-700
    • Allen, D.A.1    Tomaso, A.E.2    Priest, O.P.3    Hindson, D.F.4    Hurlburt, J.L.5
  • 22
    • 78449288692 scopus 로고    scopus 로고
    • Using NMR to Probe the Regio- and Sterochemistry of the Hydration of 1-Hexene
    • Saba, S.; Clarke, D. D.; Iwanoski, C.; Lobasso, T. Using NMR to Probe the Regio- and Sterochemistry of the Hydration of 1-Hexene J. Chem. Educ. 2010, 87, 1238-1241
    • (2010) J. Chem. Educ. , vol.87 , pp. 1238-1241
    • Saba, S.1    Clarke, D.D.2    Iwanoski, C.3    Lobasso, T.4
  • 24
    • 80051679393 scopus 로고    scopus 로고
    • Determination of Absolute Configuration Using Kinetic Resolution Catalysts
    • 1H NMR spectroscopy, see - 4473
    • 1H NMR spectroscopy, see: Wagner, A. J.; David, J. G.; Rychnovsky, S. D. Determination of Absolute Configuration Using Kinetic Resolution Catalysts Org. Lett. 2011, 13, 4470-4473
    • (2011) Org. Lett. , vol.13 , pp. 4470
    • Wagner, A.J.1    David, J.G.2    Rychnovsky, S.D.3
  • 25
    • 84873332192 scopus 로고    scopus 로고
    • Absolute Configuration of Lactams and Oxazolidinones Using Kinetic Resolution Catalysts
    • 1H NMR spectroscopy, see - 475
    • 1H NMR spectroscopy, see: Perry, M. A.; Trinidad, J. V.; Rychnovsky, S. D. Absolute Configuration of Lactams and Oxazolidinones Using Kinetic Resolution Catalysts Org. Lett. 2013, 15, 472-475
    • (2013) Org. Lett. , vol.15 , pp. 472
    • Perry, M.A.1    Trinidad, J.V.2    Rychnovsky, S.D.3
  • 26
    • 84871377901 scopus 로고    scopus 로고
    • Nanomole-Scale Assignment of Configuration for Primary Amines Using a Kinetic Resolution Strategy
    • For the CEC method with primary amines using mass spectrometry, see: Miller, S. M.; Samame, R. A.; Rychnovsky, S. D. Nanomole-Scale Assignment of Configuration for Primary Amines Using a Kinetic Resolution Strategy J. Am. Chem. Soc. 2012, 134, 20318-20321
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 20318-20321
    • Miller, S.M.1    Samame, R.A.2    Rychnovsky, S.D.3
  • 27
    • 84877140970 scopus 로고    scopus 로고
    • Determination of Absolute Configuration of Secondary Alcohols Using Thin-Layer Chromatography
    • For the CEC method with secondary alcohols using thin-layer chromatography, see - 4598
    • For the CEC method with secondary alcohols using thin-layer chromatography, see: Wagner, A. J.; Rychnovsky, S. D. Determination of Absolute Configuration of Secondary Alcohols Using Thin-Layer Chromatography J. Org. Chem. 2013, 78, 4594-4598
    • (2013) J. Org. Chem. , vol.78 , pp. 4594
    • Wagner, A.J.1    Rychnovsky, S.D.2
  • 28
    • 0002124835 scopus 로고
    • Determination of the Configuration of Secondary Alcohols by Partial Resolution
    • Fiaud, J. Horeau, A. Kagan, H. B. Georg Thieme: Stuttgart, Vol. - 94
    • Horeau, A. Determination of the Configuration of Secondary Alcohols by Partial Resolution. In Stereochemistry, Fundamentals and Methods; Fiaud, J.; Horeau, A.; Kagan, H. B., Eds.; Georg Thieme: Stuttgart, 1977; Vol. 3, pp 51-94.
    • (1977) Stereochemistry, Fundamentals and Methods , vol.3 , pp. 51
    • Horeau, A.1
  • 29
    • 45549099652 scopus 로고    scopus 로고
    • Homobenzotetramisole: An Effective Catalyst for Kinetic Resolution of Aryl-Cycloalkanols
    • Birman, V. B.; Li, X. Homobenzotetramisole: An Effective Catalyst for Kinetic Resolution of Aryl-Cycloalkanols Org. Lett. 2008, 10, 1115-1118
    • (2008) Org. Lett. , vol.10 , pp. 1115-1118
    • Birman, V.B.1    Li, X.2
  • 30
    • 84900549013 scopus 로고    scopus 로고
    • The HBTM catalyst is commercially available from Sigma-Aldrich (R-HBTM, L511730; S-HBTM, L511862)
    • The HBTM catalyst is commercially available from Sigma-Aldrich (R-HBTM, L511730; S-HBTM, L511862).
  • 31
    • 0032472401 scopus 로고    scopus 로고
    • Enantioselectivity of Candida antarctica lipase for some synthetic substrates including aliphatic secondary alcohols
    • Both enantiomers of compounds 1, 2, and 3 were synthesized based on the following procedure - 60
    • Both enantiomers of compounds 1, 2, and 3 were synthesized based on the following procedure: Ohtani, T.; Nakatsukasa, H.; Kamezawa, M.; Tachibana, H.; Naoshima, Y. Enantioselectivity of Candida antarctica lipase for some synthetic substrates including aliphatic secondary alcohols J. Mol. Catal. B: Enzym. 1998, 4, 53-60
    • (1998) J. Mol. Catal. B: Enzym. , vol.4 , pp. 53
    • Ohtani, T.1    Nakatsukasa, H.2    Kamezawa, M.3    Tachibana, H.4    Naoshima, Y.5
  • 32
    • 84900533387 scopus 로고    scopus 로고
    • ImageJ spot-density program can be downloaded free of charge at (accessed Mar). There is a tutorial video for the students hosted on the UCIReplay servers. http://replay.uci.edu/media/public/spring2013/How-to-use-ImageJ-Flash- %28Large%29-20130425-10.12.58PM.html (accessed Mar)
    • ImageJ spot-density program can be downloaded free of charge at http://rsbweb.nih.gov/ij/ (accessed Mar 2014). There is a tutorial video for the students hosted on the UCIReplay servers. http://replay.uci.edu/media/public/ spring2013/How-to-use-ImageJ-Flash-%28Large%29-20130425-10.12.58PM.html (accessed Mar).
    • (2014)
  • 33
    • 54249095628 scopus 로고    scopus 로고
    • 3-PIP-Catalyzed Kinetic Resolution of Secondary Benzylic Alcohols
    • 3-PIP-Catalyzed Kinetic Resolution of Secondary Benzylic Alcohols J. Am. Chem. Soc. 2008, 130, 13836-13837
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 13836-13837
    • Li, X.1    Liu, P.2    Houk, K.N.3    Birman, V.B.4
  • 34
    • 84887068083 scopus 로고    scopus 로고
    • Kinetic Analysis of the HBTM-Catalyzed Esterification of an Enantiopure Secondary Alcohol
    • For a detailed kinetic study with the HBTM catalyst, see - 5507
    • For a detailed kinetic study with the HBTM catalyst, see: Wagner, A. J.; Rychnovsky, S. D. Kinetic Analysis of the HBTM-Catalyzed Esterification of an Enantiopure Secondary Alcohol Org. Lett. 2013, 15, 5504-5507
    • (2013) Org. Lett. , vol.15 , pp. 5504
    • Wagner, A.J.1    Rychnovsky, S.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.