GSC  Vol.1 No.1 , February 2011
Resolution of Alcohol Racemate by Oil
Abstract: Vegetable oil was successfully used as solvent and acyl donor in the kinetic resolution of several secondary alcohol racemates yielding high enantioselectivities. Using vegetable oil as solvent and acyl donor allowed easy separation of the pure alcohol enantiomer by extraction with methanol, by distillation under reduced pressure, or by column chromatography.
Cite this paper: nullA. Wolfson, N. Komyagina, C. Dlugy and J. Blumenfeld, "Resolution of Alcohol Racemate by Oil," Green and Sustainable Chemistry, Vol. 1 No. 1, 2011, pp. 7-11. doi: 10.4236/gsc.2011.11002.

[1]   R. A. Sheldon, “Chirotechnology: Industrial Synthesis of Optically Active Compounds,” Marcel Dekker, New York, 1993.

[2]   A. N. Collins, G. Sheldarke and J. Crosby, “Chirality in Industry: The Commercial Manufacture and Application of Optically Active Compounds,” John Wiley, New York, 1995.

[3]   A. Baiker, “Progress in Asymmetric Heterogeneous Catalysis: Design of Novel Chirally Modified Platinum Metal Catalysts,” Journal of Molecular Catalysis A: Chemical, Vol. 115, No. 3, 1997, pp. 473-493. doi:10.1016/S1381-1169(96)00352-4

[4]   E. Santaniello, P. Ferrabosc, P. Grisenti and A. Manzocchi, “The Biocatalytic Approach to the Prepara- tion of Enantiomerically Pure Chiral Building Blocks,” Chemical Reviews, Vol. 92, No. 5, 1992, pp. 1071-1140. doi:10.1021/cr00013a016

[5]   D. M. Tsachen, L. M. Fuentes J. E. Lynch, W. L. Laswell, R. P. Volante and I. Shinkai, “An Efficient Synthesis of 4-benzoyloxyazetidinone: An Important Carbapenem Intermediate,” Tetrahedron Letters, Vol. 29, No. 23, 1988, pp. 2779-2782.

[6]   K. Mori, “Synthesis of Optically Active Pheromones,” Tetrahedron, Vol. 45, No. 11, 1989, pp. 3233-3298. doi:10.1016/S0040-4020(01)81007-3

[7]   C. Dhenaut, I. Ledoux, I. D. W. Samuel, J. Zyss, M. Bourgault and H. Le Bozec, “Chiral Metal Complexes with Large Octupolar Optical Nonlinearities,” Nature, Vol. 374, 1995, pp. 339-342. doi:10.1038/374339a0

[8]   L. Poppe and L. Novak, “Selective Biocatalysis,” VCH, Weinheim, 1992.

[9]   L. H. Pignolet, “Homogeneous Catalysis with Metal Phosphine Complexes,” Plenume Press, New York, 1983.

[10]   R. Noyori, “Asymmetric Catalysis in Organic Synthesis,” John Wiley, New York, 1994.

[11]   E. E. Jacobsen, L. S. Andresen and T. Anthonsen, “Immobilization Does Not Influence the Enantioselectivity of CAL-B Catalyzed Kinetic Resolution of Secondary Slcohols,” Tetrahedron: Asymmetry, Vol. 16, No. 4, 2005, pp. 847-850. doi:10.1016/j.tetasy.2004.11.081

[12]   E. E. Jacobsen, E. W. van Hellemond, A. R. Moen, L. C. V. Prado and T. Anthonsen, “Enhanced Selectivity in Novozym 435 Catalyzed Kinetic Resolution of Secon- dary Alcohols and Butanoates Caused by the (R)-alcohols,” Tetrahedron Letters, Vol. 44, No. 46, 2003, pp. 8453-8455. doi:10.1016/j.tetlet.2003.09.105

[13]   N. Kim, S. B. Ko, M. S. Kwon, M. J. Kim and J. Park, “Air-Stable Racemization Catalyst for Dynamic Kinetic Resolution of Secondary Alcohols at Room Tempe- rature,” Organic Letters, Vol. 7, No. 20, 2005, pp. 4523-4526. doi:10.1021/ol051889x

[14]   B. Martin-Matute, E. Michaela, K. Bogár, F. B. Kaynak and J. E. B?ckvall, “Combined Ruthenium(II) and Lipase Catalysis for Efficient Dynamic Kinetic Resolution of Secondary Alcohols. Insight into the Racemization Mechanism,” Journal of the American Chemical Society, Vol. 127, No. 24, 2005, pp. 8817-8825. doi:10.1021/ja051576x

[15]   C. Dlugy and A. Wolfson, “Lipase Catalyse Glycerolysis for Kinetic Resolution of Racemates,” Bioprocess and Biosystems Engineering, Vol. 30, No. 5, 2006, pp. 327-330. doi:10.1007/s00449-007-0128-x

[16]   A. Ballesteros, U. Bornscheuer, A. Capewell, D. Combes, J. S. Condoret and K. Koenig, “Review Article Enzymes in Non-Conventional Phases,” Biocatalysis and Biotrans- formation, Vol. 13, No. 1, 1995, pp. 1-42. doi:10.3109/10242429509040103

[17]   E. R. Sherwin, “Antioxidants for Vegetable Oils,” Journal of the American Oil Chemists’ Society, Vol. 53, No. 6, 1976, pp. 430-436. doi:10.1007/BF02605739