The Journal of Organic Chemistry
Article
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Table 2. H Chemical Shift Differences between
ACKNOWLEDGMENTS
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Diastereomers Measured at 400 MHz for Racemic Mixtures
N.S. gratefully acknowledges the financial aid for this work by
the Department of Science and Technology, New Delhi, for
Grant No. SR/S1/PC-32/2008, and S.R.C. thanks UGC, New Delhi,
for SRF. Nilamoni Nath and Sankeerth Hebbar are thanked for
helpful discussions.
a
of 7−14
REFERENCES
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(1) (a) Gubitz, G., Schmid, M. G., Eds. Chiral Separations: Methods
̈
and Protocols (Methods in Molecular Biology); Humana Press Inc.:
Totowa, NJ, 2010. (b) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed.
1998, 37, 1020. (c) Gawley, R. E.; Aube, J. Principles of Asymmetric
Synthesis; Pergamon: Oxford, U.K., 1996. (d) Dewick, P. M. Medicinal
Natural Products: A Biosynthetic Approach; John Wiley and Sons:
Chichester, U.K., 2001. For a recent review, please see: (e) Hembury,
G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1. For recent
examples of chiral recognition by synthetic receptors, please see:
(f) Ema, T.; Tanida, D.; Sakai, T. J. Am. Chem. Soc. 2007, 129, 10591.
(g) Miyaji, H.; Hong, S.-J.; Jeong, S.-D.; Yoon, D.-W.; Na, H.-K.; Ham,
S.; Sessler, J. L.; Lee, C.-H. Angew. Chem., Int. Ed. 2007, 46, 2508.
(h) Gasparrini, F.; Pierini, M.; Villani, C.; Filippi, A.; Speranza, M.
J. Am. Chem. Soc. 2008, 130, 522.
(2) (a) Ward, T. J.; Hamburg, D.-M. Anal. Chem. 2004, 76, 4635.
(b) Ward, T. J.; Ward, K. D. Anal. Chem. 2010, 82, 4712.
(3) (a) Rothchild, R. Enantiomer 2000, 5, 457. (b) Seco, J. M.; Quinoa,
E.; Riguera, R. Tetrahedron: Asymmetry 2001, 12, 2915. (c) Seco, J. M.;
Quinoa, E.; Riguera, R. Chem. Rev. 2004, 104, 17. (d) Wenzel, T. J.;
Wilcox, J. D. Chirality 2003, 15, 256. (e) Wenzel, T. J. Discrimination of
Chiral Compounds Using NMR Spectroscopy; Wiley: Hoboken, NJ, 2007.
(f) Wenzel, T. J.; Chisholm, C. D. Prog. Nucl. Magn. Reson. Spectrosc.
2011, 59, 1.
(4) (a) Port, A.; Virgili, A.; Jaime, C. Tetrahedron: Asymmetry 1996, 7,
1295. (b) Port, A.; Virgili, A.; Larena, A. A.; Piniella, J. F. Tetrahedron:
Asymmetry 2000, 11, 3747. (c) Enders, D.; Thomas, C. R.; Runsink, J.
Tetrahedron: Asymmetry 1999, 10, 323. (d) Yang, X.; Wang, G.; Zhong,
C.; Wu, X.; Fu, E. Tetrahedron: Asymmetry 2006, 17, 916. (e) Cuevas,
́
F.; Ballester, P.; Pericas, M. A. Org. Lett. 2005, 7, 5485. (f) Fulwood,
R.; Parker, D. J. Chem. Soc., Perkin Trans. 2 1994, 57. (g) Staubach, B.;
Buddrus, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1344. (h) Bailey, D. J.;
O’Hagan, D.; Tavasli, M. Tetrahedron: Asymmetry 1997, 8, 149. (i) Yang,
D.; Li, X.; Fan, Y.-F.; Zhang, D.-W. J. Am. Chem. Soc. 2005, 127, 7996.
(j) Bilz, A.; Stork, T.; Helmchen, G. Tetrahedron: Asymmetry 1997, 8,
3999.
́
(5) (a) Seco, J. M.; Latypov, Sh. K.; Quinoa, E.; Riguera, R. J. Org.
̃
Chem. 1997, 62, 7569. (b) Kusumi, T.; Fukushima, T.; Ohtani, I.;
Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939.
(6) (a) Wenzel, T. J.; Thurston, J. E. J. Org. Chem. 2000, 65, 1243.
(b) Wenzel, T. J.; Freeman, B. E.; Sek, D. C.; Zopf, J. J.; Nakamura, T.;
Yongzhu, J.; Hirose, K.; Tobe, Y. Anal. Bioanal. Chem. 2004, 378,
1536. (c) Machida, Y.; Kagawa, M.; Nishi, H. J. Pharm. Biomed. Anal.
2003, 30, 1929.
(7) (a) Perez-Fuertes, Y.; Kelly, A. M.; Fossey, J. S.; Powell, M. E.; Bull,
S. D.; James, T. D. Nat. Protoc. 2008, 3, 210−214. (b) Perez-Fuertes, Y.;
Kelly, A. M.; Johnson, A. L.; Arimori, S.; Bull, S. D.; James, T. D. Org.
Lett. 2006, 8, 609. (c) Kelly, A. M.; Perez-Fuertes, Y.; Arimori, S.; Bull,
S. D.; James, T. D. Org. Lett. 2006, 8, 1971. (d) Kelly, A. M.; Perez-Fuertes,
Y.; Fossey, J. S.; Yeste, S. L.; Bull, S. D.; James, T. D. Nat. Protoc. 2008, 3,
215. (e) Kelly, A. M.; Bull, S. D.; James, T. D. Tetrahedron: Asymmetry
2008, 19, 489. (f) Axe, P.; Bull, S. D.; Davidson, M. G.; Gilfillan, C. J.;
Jones, M. D.; Robinson, D. E. J. E.; Turner, L. E.; Mitchell, W. L. Org.
Lett. 2007, 9, 223. (g) Taylor, P. J. M.; Bull, S. D. Tetrahedron:
Asymmetry 2006, 17, 1170.
a
Note: protons a and b are marked in Scheme 2. Other protons are
marked in the respective figures.
ASSOCIATED CONTENT
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* Supporting Information
The H and 19F spectra of the investigated molecules. This
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material is available free of charge via the Internet at http://
AUTHOR INFORMATION
Corresponding Author
*Tel: ++91 80 22933300. Fax: ++91 80 23601550. E-mail: nsp@
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dx.doi.org/10.1021/jo202334d | J. Org. Chem. 2012, 77, 648−651