Recent NMR methodological developments for chiral analysis in isotropic solutions

Journal of the Indian Institute of Science

Volumn 94, Issue 4, 2014, Pages 485-516

  Chaudhari, Sachin Rama ^a   Suryaprakash, N ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL SHIFT; ENANTIOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROSCOPIC ANALYSIS;

CHIRAL AUXILIARIES; EXPERIMENTAL METHODOLOGY; FREQUENCY-SELECTIVE; ISOTROPIC SOLUTIONS; NMR EXPERIMENTS; OVERLAPPED PEAKS; QUANTUM DETECTION; SPECTROSCOPIC STUDIES;

STEREOCHEMISTRY;

EID: 84911012882     PISSN: 09704140     EISSN: 00194964     Source Type: Journal    
DOI: None     Document Type: Article

References (147)

1. Eliel, E. L., (1962) Stereochemistry of Carbon Compounds, McGraw-Hill Book Co.
2. Morris, D. G., (2001) Stereochemistry, The Royal Society of Chemistry, Cambridge.
3. Robinson, M. J. T., (2001) Organic Stereochemistry (Oxford Chemistry Primers), Oxford University Press, New York.
4. Kalsi, P. S., (2005) Stereochemistry, Conformation and Mechanism 6th Edition, New Age International Pvt. Ltd., New Delhi.
5. Cahn, R. S., Ingold C and Prelog V. (1966) Angew. Chem. Int. Ed. Engl., 5, 385.
6. Cahn, R. S. and Ingold C. K., (1951) J. Chem. Soc. 612.
7. IUPAC Commission on Nomenclature of Organic Chemistry, 1974 recommendations for section E, Fundamental Stereochemistry, (1976) Pure Appl. Chem., 45, 11.
8. Nasipuri, D., (2009) Stereochemistry of Organic Compounds, Principles and Applications, 2nd Edition, New Age International (P) Ltd.
9. Gupta, S. S., (1997) Basic Stereochemistry of Organic Molecule, Book Syndicate Private Ltd.
10. Cairns, D., (2008) Essentials of Pharmaceutical Chemistry, Third edition, Pharmaceutical Press, USA.
11. Ikai, T., Okamoto Y. (2009) Chem. Rev. 109, 6077.
12. Parker, D., (1991) Chem. Rev., 91, 1441.
13. Dunitz, J. D., (1995) X-Ray Analysis and the Structure of Organic Molecules, 2nd Corrected Reprint; Verlag Helvetica Chimica Acta, Basel and VCH: New York.
14. Harada, N., Nakanishi K. (1983) Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry, University Science Book: Mill Valley, CA.
15. Minick, D. J., Copley, R. C. B., Szewczyk, J. R., Rutkowske, R. D., Miller, L. A., (2007) Chirality, 19, 731.
16. Stephens, P. J., Pan, J. J., Krohn, K., (2007) J. Org. Chem., 72, 7641.
17. Ward, T. J., Hamburg, D. M., (2004) Anal. Chem., 76, 4635.
18. Ward, T. J., Ward, K. D., (2010) Anal. Chem., 82, 4712.
19. Sekhon, B. S., Int. J. Pharm Tech. Res., (2010) 2, 1584-1594.
20. Mateos, J. L., Cram, D. J., (1959) J. Am. Chem. Soc., 81, 2756.
21. Wenzel, T. J., (2007) Discrimination of Chiral Compounds Using NMR Spectroscopy, Wiley Interscience, Hoboken, NJ.
22. Seco, J. M., Quinoa, E., Riguera, R., (2004) Chem. Rev. 104, 17.
23. Wenzel, T. J., Chisholm, C. D., (2011) Prog. Nucl. Magn. Reson. Spectrosc. 59, 1.
24. Sarfati, M., Lesot, P., Merlet, D., Courtieu, J., (2000) Chem. Commun. 2069.
25. Lokesh, Suryaprakash, N., (2013) Chem. Comm., 49, 2049.
26. Lokesh, Suryaprakash, N., (2012) Chem. Eur. J., 18, 11560.
27. Reddy, U. V., Suryaprakash, N., (2011) Chem. Comm., 47, 8364.
28. Luy, B., Kobzar, K., Kessler, H., (2004) Angew. Chem. 116, 1112;
29. Angew. Chem. Int. Ed. (2004) 43, 1092.
30. Luy, B., Kobzar, K., Knör, S., Furrer, J., Heckmann, D., Kessler, H., (2005) J. Am.Chem. Soc.127, 6459.
31. Kummerlöwe, G., Knör, S., Frank, A. O., Paululat, T., Kessler, H., Luy, B., (2008) Chem. Commun. 44, 5722.
32. Luy, B., (2010) J. Ind. Inst. Sci., 90, 119 and references therein.
33. Meddour, A., Canet, I., Loewenstein, A., Pechine, J. M., Courtieu, J., (1994) J. Am. Chem. Soc., 116, 9652.
34. Chalard, P., Bertrand, M., Canet, I., Thery, V., Remuson, R., Jaminet, G., (2000) Org. Lett., 2, 2431.
35. Lesot, P., Courtieu, J., (2009) Prog. Nucl. Magn. Reson. Spectrosc. 55, 128.
36. Raban, M., Mislow, K., (1965) Tetrahedron Lett., 48, 4249.
37. Pirkle, W. H., (1966) J. Am. Chem. Soc., 88, 1837.
38. Jeffrey, G. A., (1997) An Introduction to Hydrogen Bonding, Oxford University Press, Oxford.
39. Schneider, H.-J., Yatsimirsky A., (2000) Principles and Methods in Supramolecular Chemistry, Wiley, New York.
40. Pirkle, W. H., Hoover, D. J., (1982) Top. Stereochem. 13, 263.
41. Hinckley, C. C., (1969) J. Am. Chem. Soc., 91, 5160.
42. Farjon, J., Baltaze J. P., Lesot P., Merlet D., Courtieu (2004) J. Magn. Reson. Chem., 42, 594.
43. Dale, J. A., Mosher H. S. (1973) J. Am. Chem. Soc., 95, 512.
44. Dale, J. A., Dull D. L., Mosher H. S., (1969) J. Org. Chem., 34, 2543.
45. Uccello-Barretta, G., Bernardini, R., Balzano, F., Salvadori, P., (2002) Chirality, 14, 484.
46. Nieto, S., Cativiela, C., Urriolabeiti, E. P., (2012) New J. Chem., 36, 566.
47. Rodriguez-Escrich, S., Popa, D., Jimeno, C., Vidal-Ferran, A., Pericas, M. A., (2005) Org. Lett., 7, 3829.
48. Orlov, N. V., Ananikov, V. P., (2010) Chem. Commun., 46, 3212 and references therein.
49. Nath, N. and Suryaprakash, N., (2010) J. Magn. Reson, 202, 34.
50. Uday, R. P., Bikash, B., Suryaprakash, N., (2008) J. Phys. Chem. A., 112, 5658.
51. Uday, R. P., Suryaprakash, N., (2008) J. Magn. Reson., 195, 145.
52. Uday, R. P., Suryaprakash, N., (2010) J. Magn. Reson. 202, 217.
53. Aue, W. P., Karhan, J., Ernst, R. R., (1976) J. Chem. Phys. 64, 4226.
54. Farjon, J., Merlet, D., Lesot, P., and Courtieu, J., (2002) J. Magn. Reson. 158, 169.
55. Uday, R. P., Bikash, B., Suryaprakash, N. (2008) J. Magn. Reson. 191, 259.
56. Giraud, N., Joos, M., Courtieu, J., Merlet D., (2009) Magn. Reson. Chem. 47, 300.
57. Uday, R. P., Suryaprakash, N., (2010) J. Phys. Chem. A, 114, 5551.
58. Nath, N., Kumari, D., Suryaprakash, N., (2011) Chem. Phys. Letts. 508, 149.
59. Oliver, M., Bach II, A., Balibar, C., Byrne, N., Cai, Y., Carter, G., Chlenov, M., Di, L., Fan, K., Goljer, I., He, Y., Herold, D., Kagan, M., Kerns, E., Koehn, F., Kraml, C., Marathias, V., Marquez, B., McDonald, L., Nogle, L., Petucci, C., Schlingmann, G., Tawa, G., Tischler, M., Williamson, R. T., Sutherland, A., Watts, W., Young, M., Zhang, M.Y, Zhang, Y., Zhou, D. and Ho, D., (2007) Chirality, 19, 658.
60. Klika, K. D., (2009) Tetrahedron: Asymm., 20, 1099.
61. Lovely, A. E., T. Wenzel, (2006) Org. Lett., 8, 2823.
62. Lokesh, Chaudhari, S. R. and Suryaprakash, N., Org. Biomol. Chem., (2014) 12, 993.
63. Wenzel, T. J. and Chisholm, C. R., (2011) Chirality, 23, 190.
64. Seco, J. M., Quiñoá, E., Riguera, R., (2012) Chem. Rev., 112, 4603.
65. Seco, J. M., Quiñoá E., R. Riguera, (2004) Chem. Rev., 104, 17.
66. Pérez-Fuertes, Y., Kelly, A. M., Johnson, A. L., Arimori, S., Bull, S. D., and James, T. D., (2006) Org. Lett., 8, 609.
67. Chaudhari, S. R. and Suryaprakash, N., (2012) J. Org. Chem., 77, 648.
68. Chaudhari, S. R. and Suryaprakash, N., (2012) Org. Biomol. Chem., 10, 6410.
69. Tanaka, K., Ootani, M., Toda, F., (1992) Tetrahedron: Asymmetry, 3, 709.
70. Toda, F., Mori, K., Sato, A., (1988) Bull. Chem. Soc. Jpn., 61, 4167.
71. Lovely, A. E., Wenzel, T. J., (2006) J. Org. Chem., 71, 9178.
72. Wenzel, T. J., (1978) NMR Shift Reagents, CRC Press, Inc: Boca Raton, FL.
73. McCreary, M. D., Lewis, D. W., Wernick, D. L., Whitesides, G. M., (1974) J. Am. Chem. Soc. 96, 1038.
74. Cuevas, F., Ballester, P., Pericás, M. A. (2005) Org. Lett., 7, 5485.
75. Yang, D., Li, X., Fan, Y. F., Zhang, D.W., (2005) J. Am. Chem. Soc. 127, 7996.
76. Kumari, D., Hebbar, S., Suryaprakash, N., (2013) RSC Adv., 3, 3071.
77. Braunschweiler, L., Bodenhausen, G. and Ernst, R.R., (1983) Mol. Phys., 48, 535.
78. Norwood, T. J., (1992) Prog. NMR Spectroscopy, 24, 295.
79. Bodenhausen, G., (1980) Prog. NMR Spectrosocpy, 14, 137.
80. Warren, W. S., Pines, A., (1981) J. Am. Chem. Soc., 103, 1613.
81. Warren, W. S., Murdoch, J. B., Pines, A., (1984) J. Magn. Reson., 60, 236.
82. Warren, W. S., Pines A., (1981) J. Chem. Phys., 74, 2808.
83. Warren, W. S., Pines, A. (1982) Chem. Phys. Letts., 88, 441.
84. Weitekamp, D. P., Garbow, J. R., Pines, A., (1982) J. Chem. Phys., 77, 2870.
85. Murdoch, J. B., Warren, S. W., Weitekamp, D. P., Pines, A., (1984) J. Magn. Reson., 60, 205.
86. Munowitz, M., Pines, A., (1986) Science, 233, 525.
87. Murali, N., Ramakrishna, Y. V. S., Chandrasekhar, K., Thomas, M. A., and Kumar, A., (1984) Pramana, 23, 547.
88. Permi, P., Annila, A., (2000) J. Biomol. NMR, 16, 221.
89. Meissner, A., Duus, J. O., and Sorensen, O. W., (1997) J. Magn. Reson., 128, 92.
90. Meissner, A., Duus, J. O., and Sorensen, O.W., (1997) J. Biomol. NMR, 10, 89.
91. Sorensen, M. D., Meissner, A., Sorensen, O.W., (1997) J. Biomol. NMR, 10, 181.
92. Meissner, A., Herbrüggen, T. S., Sorensen, O. W., (1998) J. Am.Chem. Soc., 120, 3803.
93. Briand, J., Sorensen, O. W. (1998) J. Magn. Reson., 135, 44.
94. Nolis, P., and Parella, T., (2007) J. Biomol. NMR, 37, 65.
95. Duma, L., Hediger, S., Lesage, A. and Emsley, L., (2003) J. Magn. Reson., 164, 187.
96. Nolis, P., Espinosa, J. F., Parella, T., (2006) J. Magn. Reson., 180, 39.
97. Parella, T, Gairi, M., (2004) J. Am. Chem. Soc., 126, 9821.
98. Guichard, G., Violette, A., Chassaing, G., Miclet, E., (2008) Magn. Reson. Chem., 46, 918.
99. Rexroth, A., Schmidt, P., Szalma, S., Geppert, T., Schwalbe, H., Griesinger, C., (1995) J. Am. Chem. Soc., 117, 10389.
100. Anderson, P., Weigelt, J., Otting, G., (1988) J. Biomol. NMR, 12, 435.
101. Brutscher, B., (2001) J. Magn. Reson., 151, 332.
102. Permi, P., (2003) J. Magn. Reson., 163, 114.
103. Duma, L., Hediger, S., Brutscher, B., Böckmann, A., and Emsley, L., (2003) J. Am. Chem. Soc., 125, 11816.
104. Verel, R., Manolikas, T., Siemer, A. B., Meier, B. H., (2007) J. Magn. Reson., 184, 322.
105. Permi, P., Annila, A., (2001) J. Biomol. NMR, 20, 127.
106. Permi, P., (2002) J. Biomol. NMR. 22, 27.
107. Lee, D., Vögeli, B., Pervushin, K., (2005) J. Biomol. NMR, 31, 273.
108. Würtz, P., Fredriksson, K., Permi, P., (2005) J. Biomol. NMR, 31, 321.
109. Rani, G. C. R., Riek, R., (2003) J. Am.Chem. Soc., 125, 16104.
110. Vasos, P. R., Hall, J. B., Fushmann, D., (2005) J. Biomol. NMR, 31, 149.
111. Bikash, B, Suryaprakash, N. J. (2007) Chem. Phys. 127, 214510.
112. Lesot, P., Merlet, D., Courtieu, J., Emsley, J. W., (1996) Liq. Cryst. 21 427.
113. Bikash, B., Uday R. P., Suryaprakash, N., (2007) J. Phys. Chem. B, 111, 12403.
114. Bikash, B., Uday, R.P., Suryaprakash, N., (2008) J. Magn. Reson, 192, 101.
115. Bikash, B., Uday, R.P., Suryaprakash, N., (2008) J. Magn. Reson, 192, 92.
116. Nath, N., Bikash, B., Suryaprakash, N. (2009) J. Magn. Reson, 200, 101.
117. Bikash, B., Uday, R.P., Suryaprakash, N., (2009) Ann. Rep. NMR Spectroscopy, Graham A. Webb., The Netherlands: Elsevier, 67, 331.
118. Sweeting, L. M., Crans, D. C., Whitesides, G. M. (1987) J. Org. Chem., 52, 2273.
119. Weitekamp, D. P. (1983) Adv. Magn. Reson. 11, 111.
120. Weitekamp, D. P., Garbow J. R., Pines, A. (1982) J. Magn. Reson. 46, 529.
121. Sorenson, O. W., Levitt M. H., Ernst R. R., (1983) J. Magn. Reson. 55, 104.
122. Rance, M., Sørensen, O. W., Leupin, W., Kogler, H., Wüthrich, K., Ernst R. R., (1985) J. Magn. Reson. 61, 67.
123. Munowitz, M., Pines, A., (1987) Adv. Chem. Phys. 66, 1.
124. Barbara, T. M., Tycko, R., Weitekamp, D. P., (1985) J. Magn. Reson., 62, 54.
125. Nath, N., Suryaprakash, N., (2011) Chem. Phys. Letts., 502, 136.
126. Chaudhari, S. R., Suryaprakash, N., (2013) Chem. Phys. Letts. 555, 286.
127. Claridge, T. D. W., (2009) High-Resolution NMR Techniques in Organic Chemistry, Tetrahedron Organic Chemistry Series, Vol. 27, Second Ed.
128. Wenzel, T. J., Ciak, J. M., (2004) Electronic Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd: Sussex, UK.
129. Yang, X., Wang, G., Zhong, C., Wu, X., Fu, E., (2006) Tetrahedron: Asymm.,17, 916.
130. Yang, D., Li X., Fan, Y. F., Zhang, D. W., (2005) J. Am. Chem. Soc., 127, 7996.
131. Svatos, A., Valterova, I., Saman, D., Vrkoc, J., (1990) Chem. Commun., 55, 485.
132. Aguilar, J. A., Faulkner, S., Nilsson, M., Morris, G. A., (2010) Angew. Chem. Int. Ed., 49, 3901.
133. Aguilar, J. A., Nilsson, M., Morris, G. A., (2011) Angew. Chem. Int. Ed., 50, 9716.
134. Nilsson, M., Morris, G. A., (2007) Chem. Commun., 933.
135. Morris, G. A., Aguilar, J. A., Evans, R., Haiber, S., Nilsson, M., (2010) J. Am. Chem. Soc., 132, 12770.
136. Paudel, L., Adams, R. W., Király, P., Aguilar, J. A., Foroozandeh, M., Cliff, M. J., Nilsson, M., Sándor, P., Waltho, J. P., Morris, G. A., (2013) Angew. Chem. Int. Ed., 125, 11830.
137. Adams, R.W., Byrne L., Király P., Foroozandeh M., Paudel L., Nilsson M., Clayden J., Morris, G. A., (2014) Chem. Comm., 50, 2512.
138. Aquilar, J. A., Morris, G. A., Kenwright, A. M., (2014) RSC Adv.,4, 8278.
139. Zangger, K., Sterk, H., (1997) J. Magn. Reson., 124, 486.
140. Aguilar, J. A., Faulkner, S., Nilsson, M., Morris, G. A., (2010) Angew. Chem., Int. Ed., 49, 3901.
141. Giraud, N., Béguin, L., Courtieu, J., Merlet, D., (2010) Angew. Chem., Int. Ed., 49, 3481.
142. Meyer, N. H., Zangger, K. (2013) Angew. Chem., Int. Ed., 52, 7143.
143. Byrne, L., Sola' J., Boddaert, T., Marcelli, T., Adams, R. W., Morris, G. A., Clayden, J., (2014) Angew. Chem., Int. Ed., 126, 155.
144. Castañar, L., Nolis, P., Virgili, A., Parella, T., (2013) Chem. Eur. J., 19, 17283.
145. Ying, J., Roche, J., Bax, A., (2014) J. Magn. Reson., 241, 97.
146. Paudel, L., Adams, R. W., Király, P., Aguilar, J. A., Foroozandeh, M., Cliff, M. J., Nilsson, M., Sándor, P., Waltho, J. P., Morris, G. A., (2013) Angew. Chem., Int. Ed., 52, 11616.
147. Castañar L., Pérez-Trujillo, M., Nolis, P., Monteagudo, E., Virgili, A., Parella, T., (2014) ChemPhysChem, 15, 854.