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Journal of Analytical Methods in Chemistry
Volume 2012 (2012), Article ID 452949, 10 pages
Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis
1Chemistry Department, University of Lleida, 25198 Lleida, Spain
2Food Technology Department, University of Lleida, 25198 Lleida, Spain
Received 30 November 2011; Revised 4 February 2012; Accepted 15 February 2012
Academic Editor: Boryana M. Nikolova-Damyanova
Copyright © 2012 Mireia Oromí-Farrús et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- E. J. Bourne, M. Stacey, J. C. Tatlow, and R. Worrall, “Studies of trifluoroacetic acid—part 15. Further investigations on the reactions of acyl trifluoroacetates with hydroxy-compounds,” Journal of the Chemical Society, pp. 3268–3282, 1958.
- W. Walther and T. Netscher, “Design and development of chiral reagents for the chromatographic e.e. determination of chiral alcohols,” Chirality, vol. 8, no. 5, pp. 397–401, 1996.
- M. Kataoka, K. Kita, M. Wada, Y. Yasohara, J. Hasegawa, and S. Shimizu, “Novel bioreduction system for the production of chiral alcohols,” Applied Microbiology and Biotechnology, vol. 62, no. 5-6, pp. 437–445, 2003.
- J. E. Rekoske, “Chiral separations,” AIChE Journal, vol. 47, no. 1, pp. 2–5, 2001.
- V. Schurig, “Separation of enantiomers by gas chromatography,” Journal of Chromatography A, vol. 906, no. 1-2, pp. 275–299, 2001.
- Z. Juvancz and P. Petersson, “Enantioselective gas chromatography,” Journal of Microcolumn Separations, vol. 8, no. 2, pp. 99–114, 1996.
- J. Kang, D. Wistuba, and V. Schurig, “Recent progress in enantiomeric separation by capillary electrochromatography,” Electrophoresis, vol. 23, no. 22-23, pp. 4005–4021, 2002.
- B. Chankvetadze, “Combined approach using capillary electrophoresis and NMR spectroscopy for an understanding of enantioselective recognition mechanisms by cyclodextrins,” Chemical Society Reviews, vol. 33, no. 6, pp. 337–347, 2004.
- C. P. Kapnissi-Christodoulou, X. Zhu, and I. M. Warner, “Analytical separations in open-tubular capillary electrochromatography,” Electrophoresis, vol. 24, no. 22-23, pp. 3917–3934, 2003.
- G. Terfloth, “Enantioseparations in super- and subcritical fluid chromatography,” Journal of Chromatography A, vol. 906, no. 1-2, pp. 301–307, 2001.
- Y. Liu, A. W. Lantz, and D. W. Armstrong, “High efficiency liquid and super-/subcritical fluid-based enantiomeric separations: an overview,” Journal of Liquid Chromatography and Related Technologies, vol. 27, no. 7–9, pp. 1121–1178, 2004.
- N. M. Maier, P. Franco, and W. Lindner, “Separation of enantiomers: needs, challenges, perspectives,” Journal of Chromatography A, vol. 906, no. 1-2, pp. 3–33, 2001.
- S. Sponsier and M. Biedermann, “Optimization of chiral separations using capillary gas chromatography,” International Chromatography Laboratory, vol. 8, pp. A–F, 1998.
- S. C. Moldoneanu and V. David, “Chemical reactions used in derivatization. 18.3. Acetylation reactions,” Journal of Chromatography Library, pp. 569–576, 2002.
- J. S. Fritz and G. H. Schenk, “Acid-catalyzed acetylation of organic hydroxyl groups,” Analytical Chemistry, vol. 31, no. 11, pp. 1808–1812, 1959.
- G. Stork, T. Takahashi, I. Kawamoto, and T. Suzuki, “Total synthesis of prostaglandin F2α by chirality transfer from D-glucose,” Journal of the American Chemical Society, vol. 100, no. 26, pp. 8272–8273, 1978.
- K. L. Chandra, P. Saravanan, R. K. Singh, and V. K. Singh, “Lewis acid catalyzed acylation reactions: scope and limitations,” Tetrahedron, vol. 58, no. 7, pp. 1369–1374, 2002.
- M. Servrin and A. Krief, “Regioselective ad [C,C] connective routes to oxetanes and tetrahydrofuranes,” Tetrahedron Letters, vol. 21, no. 6, pp. 585–586, 1980.
- A. Orita, C. Tanahashi, A. Kakuda, and J. Otera, “Highly efficient and versatile acylation of alcohols with Bi(OTf)3 as catalyst,” Angewandte Chemie, vol. 39, no. 16, pp. 2877–2879, 2000.
- Y. Nakae, I. Kusaki, and T. Sato, “Lithium perchlorate catalyzed acetylation of alcohols under mild reaction conditions,” Synlett, no. 10, pp. 1584–1586, 2001.
- P. Phukan, “Iodine as an extremely powerful catalyst for the acetylation of alcohols under solvent-free conditions,” Tetrahedron Letters, vol. 45, no. 24, pp. 4785–4787, 2004.
- Y. Ren and C. Cai, “Molecular iodine in ionic liquid: a green catalytic system for esterification and transesterification,” Synthetic Communications, vol. 40, no. 11, pp. 1670–1676, 2010.
- M. A. Hussain, D. Shahwar, M. N. Hassan, M. N. Tahir, M. S. Iqbalc, and M. Sher, “An efficient esterification of pullulan using carboxylic acid anhydrides activated with iodine,” Collection of Czechoslovak Chemical Communications, vol. 75, no. 1, pp. 133–143, 2010.
- H. N. Cheng, M. K. Dowd, R. L. Shogren, and A. Biswas, “Iodine-catalyzed synthesis of mixed cellulose esters,” American Chemical Society, Division of Polymer Chemistry, vol. 51, pp. 29–30, 2010.
- A. K. Verma, T. Aggarwal, V. Rustagi, and R. C. Larock, “Iodine-catalyzed and solvent-controlled selective electrophilic cyclization and oxidative esterification of ortho-alkynyl aldehydes,” Chemical Communications, vol. 46, no. 23, pp. 4064–4066, 2010.
- R. A. Jones, R. Davidson, A. T. Tran, N. Smith, and M. Carmen Galan, “Iodine-catalyzed one-pot acetalation-esterification reaction for the preparation of orthogonally protected glycosides,” Carbohydrate Research, vol. 345, no. 13, pp. 1842–1845, 2010.
- K. Ramalinga, P. Vijayalakshmi, and T. N. B. Kaimal, “A mild and efficient method for esterification and transesterification catalyzed by iodine,” Tetrahedron Letters, vol. 43, no. 5, pp. 879–882, 2002.
- S. P. Chavan, K. Shivasankar, R. Sivappa, and R. Kale, “Zinc mediated transesterification of β-ketoesters and coumarin synthesis,” Tetrahedron Letters, vol. 43, no. 47, pp. 8583–8586, 2002.
- S. P. Chavan, R. R. Kale, K. Shivasankar, S. I. Chandake, and S. B. Benjamin, “A simple and efficient method for transesterification of β-ketoesters catalysed by iodine,” Synthesis, no. 17, pp. 2695–2698, 2003.
- N. Ahmed and J. E. van Lier, “Molecular iodine in isopropenyl acetate (IPA): a highly efficient catalyst for the acetylation of alcohols, amines and phenols under solvent free conditions,” Tetrahedron Letters, vol. 47, no. 30, pp. 5345–5349, 2006.
- M. Jereb, D. Vražič, and M. Zupan, “Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions,” Tetrahedron Letters, vol. 50, no. 20, pp. 2347–2352, 2009.
- IUPAC Compendium of Chemical Terminology, 2nd edition, 1997.
- I. D. Smith and C. F. Simpson, “Investigation into the GC separation of enantiomers on a trifluoroacetylated cyclodextrin—1. Effect of analyte structure on stereoselectivity for alcohols,” Journal of High Resolution Chromatography, vol. 15, pp. 800–806, 1992.
- “Chiral Cyclodextrin Capillary Columns,” Supelco Bulletin 887, 1998.
- A Guide to the Analysis of Chiral Compounds by GC, Resteck Corporation, 1997.
- M. A. Dessoy, J. De, E. M. Ethur, E. C. M. Dessoy, and A. F. Morel, “Heptakis(6-O-ethyl-2,3-O-pentyl)-β-cyclodextrin: a new chiral stationary phases for capillary GC,” HRC Journal of High Resolution Chromatography, vol. 22, no. 4, pp. 242–244, 1999.
- AIST, Integrated Spectral Database System of Organic Compounds, National Institute of Advanced Industrial Science and Technology, Japan, 2011.
- WSS: Spectral data were obtained from Wiley Subscription Services, Inc. USA.
- J. Krupcik, E. Benicka, P. Majek, I. Skacani, and P. Sandra, “Relationship between structure and chromatographic behaviour of secondary alcohols and their derivatives separated by high-resolution gas chromatography with a modified β-cyclodextrin stationary phase,” Journal of Chromatography A, vol. 665, no. 1, pp. 175–184, 1994.
- A. M. Stalcup, K. H. Ekborg, M. P. Gasper, and D. W. Armstrong, “Enantiomeric separation of chiral components reported to be in coffee, tea, or cocoa,” Journal of Agricultural and Food Chemistry, vol. 41, no. 10, pp. 1684–1689, 1993.
- C. Bicchi, A. D'Amato, V. Manzin, and P. Rubiolo, “Cyclodextrin derivatives in GC separation of racemic mixtures of volatiles—part 11. Some applications of cyclodextrin derivatives in GC enantioseparations of essential oil components,” Flavour and Fragrance Journal, vol. 12, no. 2, pp. 55–61, 1997.
- H. R. Kim, H. S. Oh, H. J. Park, J. N. Kim, D. J. Jeon, and E. K. Ryu, “A facile 1,2-acetoxychlorination reaction of olefins by using the N,N-dimethtylacetamide/hydrogen chloride/m-chloroperbenzoic acid (or oxone) system,” Synthetic Communications, vol. 28, no. 1, pp. 159–165, 1998.
- W. Y. Li, H. L. Jin, and D. W. Armstrong, “2,6-Di-O-pentyl-3-O-trifluoroacetyl cyclodextrin liquid stationary phases for capillary gas chromatographic separation of enantiomers,” Journal of Chromatography, vol. 509, no. 2, pp. 303–324, 1990.