Enantioselective epoxidation using liposomised m-chloro-perbenzoic acid (LIP MCPBA)

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4751-4754

  Kumar, Atul ^a   Bhakuni, Vinod ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; LIPOSOME;

ARTICLE; CHIRALITY; EPOXIDATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0030200250     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00925-2     Document Type: Article

References (20)

1. 1.a) Jacobsen, E.N. In Catalytic Asymmetric Synthesis, Ojima, I. Ed.: VCH: New York, 1993, Chapter 4.2.
2. b) Palucki, M.; McCormick, G.J.; Jacobsen, E.N. Tetrahedron Lett. 1995, 36, 5457-60.
3. 2.a) Allain, E.A.; Hager, L.P.; Deng, L.P.; Jacobsen, E.A. J. Am. Chem. Soc, 1995, 115, 4415-16.
4. b) Lee, N.H.; Muci, A.R.; Jacobsen, E.N. Tetrahedron Lett., 1991, 32, 5055-58;
5. c) Koch, A.; Reymond, J.-L; Lerner, R.A. J. Am Chem. Soc., 1994, 116, 803-04.
6. d) Collman, J.P., Zhang, X., Lee N.J., Uffelman E.S; Braunman, J.I. Science 1996, 251, 1404.
7. e) Corey, E.J.; Helal, C.J. Tetrahedron Asymmetry, 1993, 34, 5227-5230.
8. f) Danyang, Y.C.; Vip, M.W.; Tang, M.K.; Wong, J.H.; Zheng, Cheung, K.K. J. Am. Chem. Soc, 1996, 118 491-92.
9. 3. Singelton, W.S.; Grey, M.S.; Brown, M.L.; White, J.L. J. Am. Oil Chem. Soc., 1965, 42, 53-56.
10. 4. Bhakuni, V.; Gupta, C.M. Biochim. Biophys Acta., 1989, 982, 216-222. Briefly; 100 mg of EYPC was dissolved in small quantity of chloroform and to it was added 25 mg of m-chloroperbenzoic acid and solution evaporated resulting into the formation of a thin film. The film was dried under vacuum for 30 mins. This was suspended in 2 mL of triple distilled water and vortexed vigrously. The suspension was sonicated at 4°C for 15 mins and centrifuged at 5000 rpm for 15 mins. The supernatent containing LIP MCPBA was passed through sepharose 6B for separating free m-CPBA from liposomised. The LIP MCPBA thus obtained was used for further reaction. The maximum incorporation of m-CPBA in liposomes that was achieved was EYPC: m-CPBA, 4:1 (wt/wt).
11. 5. Allen, T.M.; Cleland, L.G. Biochim. Biophys Acta, 1980, 597, 418-26.
12. 6. a) Bhakuni, V.; Roy, R. Biochem. Pharmacol., 1994, 47, 1461-64.
13. b) Yokono, S.; Ogli, K.; Miura, S.; Ueda, I. Biochim. Biophys. Acta., 1989, 982, 300-02.
14. 7. 0.35 m mole of desired reacting molecule was dissolved in 80 ul of ethanol. To it was added 1 ml of LIP MCPBA; the concentration of ethanol should not be more than 15% in the reaction mixture as higher concentrations disrupted the liposomes. The reaction mixture was stirred at room temperature (25°C) for 2 hrs. The product, epoxide in the present case, was extracted from the reaction mixture using ethyl acetate by phase separation. The combined ethyl acetate layers were dried over anhydrous sodium sulfate and evaporated to yield the epoxide. For completion of reaction the ratio of reacting molecule to m-CPBA in LIP MCPBA should be 1:1:4. (mole /mole).
15. 8 a) McCreary, M.D.; Lewis, D.M.; Wernick, D.L.; Whitesides, G.M. J. Am. Chem. Soc., 1974, 96, 1038-54;
16. 1H NMR (CDCl3) for 1a: 3.51 (s, 3H), 3.81 (d, 1H, J=4.6 Hz), 4.23 (d, 1H, J=4.6 Hz) and 7.27-7.45 (m, 5H, Ar-H). Molecule 2a: 3.4 (d, 1H, J=4.2 Hz), 4.1 (d, 1H, J=4.2 Hz). Molecule 3: 3.0 (d, 1H, J=4.15), 3.1-3.24 (m, 1H). Molecule 4: 3.08 (dd, 1H, J=6.9 Hz and 4.0 Hz) and 2.9-3.0 (d, 1H, J=1.8 Hz). The structures of the molecules are shown in the column of product in Table 1.
17. 9. a) Bangham, A.D. Progress in Biophysics ana Molecular Biology, 1968, 18. 29-95.
18. b) Bangham, A.D.; Hill, M.W.; Miller, N.G.A. Methods in Membrane Biology, 1974, 1, 1-68.
19. c) Papahadjopoulos, D.; Kimelberg, K.K. Prog. Surface Sci., 1973, 4, 141-232.
20. 10. Fendler, J.H. In: Liposomes in Biological Systems, (John Willey and Sons, Ltd. New York, 1980), pp 87, and references therein.