Water-Promoted Kinetic Separation of trans- and cis-Limonene Oxides
Zhao-Bing Xu
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorCorresponding Author
Jin Qu
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China, Tel.: 0086-(22)-23499247Search for more papers by this authorZhao-Bing Xu
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorCorresponding Author
Jin Qu
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China, Tel.: 0086-(22)-23499247Search for more papers by this authorAbstract
The efficient hydrolytic kinetic separation of trans/cis-(R)-(+)-limonene oxides was realized in a 1:1 mixed solvent of water and 1,4-dioxane without additional catalyst. Optically pure trans-(R)-(+)-limonene oxide was recovered in high yield (77%).
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
Filename | Description |
---|---|
cjoc_201100455_sm_suppl.pdf1.2 MB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1For example, see:
- 1a Ho, T.; Chein, R.. Helv. Chim. Acta, 2006, 89, 231.
- 1b Byrne, C. M.; Allen, S. D.; Lobkovsky, E. B.; Coates, G. W.. J. Am. Chem. Soc., 2004, 126, 11404.
- 1c Grimm, E. L.; Methot, J.; Shamji, M.. Pure Appl. Chem., 2002, 75, 231.
- 1d Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B.; Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuk, K. K.. Tetrahedron Lett., 2001, 42, 5805.
- 1e Comins, D. L.; Guerra-Weltzien, L.. Tetrahedron Lett., 1996, 37, 3807.
- 1f Kido, F.; Abiko, T.; Kato, M.. J. Chem. Soc., Perkin Trans. 1, 1995, 2989.
- 1g Ho, T.; Lee, K.. Tetrahedron Lett., 1995, 36, 947.
- 1h Tius, M. A.; Kerr, M. A.. Synth. Commun., 1988, 18, 16.
- 1i Baker, R.; Borges, M.; Cooke, N. G.; Herbert, R. H.. J. Chem. Soc., Chem. Commun., 1987, 414.
- 1j Yamasaki, M.. J. Chem. Soc., Chem. Commun., 1972, 10, 606a.
- 2 Newhall, W. F.. J. Org. Chem., 1959, 24, 1673.
- 3 Steiner, D.; Ivison, L.; Goralski, C. T.; Appel, R. B.; Gojkovic, J. R.; Singaram, B.. Tetrahedron: Asymmetry, 2002, 13, 2359.
- 4 Fürst, A.; Plattner, P. A.. Helv. Chim. Acta, 1949, 32, 275.
- 5 Andrews, P. C.; Blair, M.; Fraser, B. H.; Junk, P. C.; Massi, M.; Tuck, K. L.. Tetrahedron: Asymmetry, 2006, 17, 2833.
- 6 Salles, L.; Nixon, A. F.; Russell, N. C.; Clarke, R.; Pogorzelec, P.; Cole-Hamilton, D. J.. Tetrahedron: Asymmetry, 1999, 10, 1471.
- 7 Bettadaiah, B. K.; Srinivas, P.. J. Photochem. Photobiol., A, 2004, 167, 137.
- 8 Leffingwell, J. C.; Shackelford, R. E. (R. J. Reynolds Tobacco Co.). FR 2002595, 1969.
- 9 dos Santos, A. G.; de Lima Castro, F.; Jones, J.. Synth. Commun., 1996, 26, 2651.
- 10 Blair, M.; Andrews, P. C.; Fraser, B. H.; Forsyth, C. M.; Junk, P. C.; Massi, M.; Tuck, K. L.. Synthesis, 2007, 1523.
- 11For example, see:
- 11a Horvàth, I. T.. Green Chem., 2008, 10, 1024.
- 11b Lancester, M.. Green Chemistry: An Introductory Text, Royal Society of Chemistry, Cambridge, 2002.
- 11c
Clark, J. H.;
Macquarrie, D..
Handbook of Green Chemistry & Technology, Blackwell, Oxford, 2002.
10.1002/9780470988305 Google Scholar
- 11d Matlack, A. S., Introduction to Green Chemistry, Marcel Dekker, New York, 2001.
- 11e
Anastas, P. T.;
Heine, L. G..
Green Chemical Syntheses and Processes, Eds.: T. C. Williamson, American Chemical Society, Washington, DC, 2000.
10.1021/bk-2000-0767 Google Scholar
- 11f Anastas, P. T.; Williamson, T. C., Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Oxford University Press, Oxford, 1998.
- 11g Anastas, P. T.; Warner, J. C.. Green Chemistry: Theory and Practice, Oxford University, New York, NY, 1988.
- 11h Liu, Y.; Zeng, Q.-L.; Tang, H.-Y.; Gao, S.; Yang, Z.-R.; Zhang, S.; Liu, J.-C.. Chin J. Org. Chem., 2011, 31, 986 (in Chinese).
- 12For example, see:
- 12a
Organic Reactions in Water, Ed.: U. M. Lindström, Blackwell, Oxford, UK, 2007.
10.1002/9780470988817 Google Scholar
- 12b
Grieco, P. A., Organic Synthesis in Water, Blackie Academic and Professional, London, 1998.
10.1007/978-94-011-4950-1 Google Scholar
- 12c Li, C.-J.; Chan, T.-H., Organic Reactions in Aqueous Media, Wiley, New York, 1997.
- 12d Butler, R. N.; Coyne, A. G.. Chem. Rev., 2010, 110, 6302.
- 12e Chanda, A.; Fokin, V. V.. Chem. Rev., 2009, 109, 725.
- 12f Chen, L.; Li, C.-J.. Chem. Soc. Rev., 2006, 35, 68.
- 12g Lindström, U. M.; Andersson, F.. Angew. Chem., Int. Ed., 2006, 45, 548.
- 12h Li, C.-J.. Chem. Rev., 2005, 105, 3095.
- 12i Lindström, U. M.. Chem. Rev., 2002, 102, 2751.
- 12j Breslow, R.. Acc. Chem. Res., 1991, 24, 159.
- 12k Zhang, Y.; Cheng, M.-Y.; Shang, Z.-C.. Chin J. Org. Chem., 2011, 31, 814 (in Chinese).
- 12l Zhang, M.-M.; Li, Q.; Wu, J.-R.; Wang, X.-S.. Chin J. Org. Chem., 2009, 29, 1811 (in Chinese).
- 12m Yang, M.; Yang, Q.; Chen, P.-Q.; Peng, Y.-Y.. Chin. J. Chem., 2011, 29, 499.
- 13 Rideout, D. C.; Breslow, R.. J. Am. Chem. Soc., 1980, 102, 7816.
- 14For representative work, see:
- 14a Vilotijevic, I.; Jamison, T. F.. Science, 2007, 317, 1189.
- 14b Byers, J. A.; Jamison, T. F.. J. Am. Chem. Soc., 2009, 131, 6383.
- 14c Van Dyke, A. R.; Jamison, T. F.. Angew. Chem., Int. Ed., 2009, 48, 4430.
- 14d Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B.. Angew. Chem., Int. Ed., 2005, 44, 3275.
- 14e Tiwari, S.; Kumar, A.. J. Phys. Chem. A, 2009, 113, 13685.
- 14f Shapiro, N.; Vigalok, A.. Angew. Chem., Int. Ed., 2008, 47, 2849.
- 14g Jung, Y.; Marcus, R. A.. J. Am. Chem. Soc., 2007, 129, 5492.
- 14h Zhang, H.-B.; Liu, L.; Chen, Y.-J.; Wang, D.; Li, C.-J.. Eur. J. Org. Chem., 2006, 869.
- 15a Wang, Z.; Cui, Y.-T.; Xu, Z.-B.; Qu, J.. J. Org. Chem., 2008, 73, 2270.
- 15b Xu, Z.-B.; Qu, J.. Sci. China Chem., 2011, 54, 1718.
- 15c Li, G.-X.; Qu, J.. Chem. Commun., 2010, 2653.
- 15d Wang, J.; Liang, Y.-L.; Qu, J.. Chem. Commun., 2009, 5144.
- 16 Leffingwell, J. C.; Royals, E. E.. Tetrahedron Lett., 1965, 3829.
- 17 Woolley, E. M.; Hurkot, D. G.; Hepler, L. G.. J. Phys. Chem., 1970, 74, 3908.