Efficient preparation of enantiomerically pure (E)-γ-hydroxy-α,β- unsaturated p-tolylsulfoxides using lipase-mediated acylations

Tetrahedron Asymmetry

Volumn 11, Issue 14, 2000, Pages 2991-3001

  Guerrero De La Rosa, Victor ^a   Ordóñez, Mario ^b   Llera, José Manuel ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE; TRIACYLGLYCEROL LIPASE; VINYL ACETATE;

ACYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CHEMICAL ANALYSIS; ENANTIOMER; ENZYME MECHANISM; KINETICS; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0343228771     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00257-3     Document Type: Article

References (61)

1. (a) Page, P. Organosulfur Chemistry, Synthetic and Stereochemical Aspects; Academic Press: London, 1998, Vol. 2.
2. (b) Rayner, C. M. Contemporary Organic Synthesis 1996, 3, 499.
3. (c) Carreño, C. M. Chem. Rev. 1995, 95, 1717.
4. (d) Metzner, P.; Thuillier, A. Sulfur Reagents in Organic Synthesis; Academic Press: London, 1994.
5. (e) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961.
6. (f) Solladié, G. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p. 133.
7. (g) Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds. The Chemistry of Sulfones and Sulfoxides; John Wiley & Sons: New York, 1988.
8. (a) Carreño, C. M.; García Ruano, J. L.; Urbano, A.; Remor, C. Z.; Arroyo, Y. Tetrahedron: Asymmetry 1999, 10, 4357.
9. (b) Westwell, A. D.; Rayner C. M. In Organosulfur Chemistry, Synthetic and Stereochemical Aspects; Page, P., Ed.; Academic Press: London, 1998; Vol. 2, p. 157.
10. (c) Arai, Y.; Masuda, T.; Masaki, Y.; Shiro, M. J. Chem. Soc., Perkin Trans. 1 1996, 759.
11. (d) Koizumi, T. Phosphorus, Sulphur and Silicon 1991, 55, 111.
12. (a) Hayes, P.; Maignan, C. Tetrahedron: Asymmetry 1999, 10, 1041.
13. (b) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. Nicolio, F.; Rizzo, S. Tetrahedron: Asymmetry 1999, 10, 1041.
14. (c) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry 1997, 8, 1339.
15. (d) Carreño, C. M.; Cid, M. B.; García Ruano, J. L.; Santos, M. Tetrahedron: Asymmetry 1997, 8, 2093.
16. (a) Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1997, 8, 109.
17. (b) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T. Tetrahedron: Asymmetry 1991, 2, 1379.
18. (c) Koizumi, T.; Hirai, H.; Yoshii, E. J. Org. Chem. 1982, 47, 4004.
19. (a) Carretero, J. C.; García Ruano, J. L.; Cabrejas, L. M. M. Tetrahedron: Asymmetry 1997, 8, 2215.
20. (b) Mikolajczyk, M.; Midura, W. H.; Tetrahedron: Asymmetry 1993, 4, 1515.
21. (c) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086.
22. (d) Posner, G. H. Acc. Chem. Res. 1987, 20, 72.
23. Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75.
24. (a) Sengupta, S.; Sarma, D. S.; Mondal, S. Tetrahedron: Asymmetry 1998, 9, 2311.
25. (b) Simpkins, N. S. Tetrahedron 1990, 46, 6951.
26. (c) Isobe, M.; Ichikawa, Y.; Funabashi, Y.; Mio, S.; Goto, T. Tetrahedron 1986, 42, 2863.
27. (c) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903.
28. (a) Domínguez, E.; Carretero, J. C. Tetrahedron Lett. 1993, 34, 5803.
29. (b) Carretero, J. C.; Domínguez, E. J. Org. Chem. 1993, 55, 1596.
30. (c) Jackson, R. F. W.; Standen, S. P.; Clegg, W. Tetrahedron Lett. 1991, 32, 5393.
31. (d) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 3189.
32. (e) Domínguez, E.; Carretero, J. C.; Fernández-Mayoralas, A.; Conde, S. Tetrahedron Lett. 1991, 32, 5159.
33. (f) Domínguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197.
34. (a) Carretero, J. C.; García Ruano, J. L.; Lorente, A.; Yuste, F. Tetrahedron: Asymmetry 1993, 4, 111.
35. (b) Niyazymbetov, M. E.; Konyushkin, L. D.; Niyazymbetova, Z. I.; Kalugin, V. E.; Lituinov, V. P.; Petroyan, V. A. Tetrahedron Lett. 1991, 32, 1099.
36. (c) Solladié, G.; Moine, G. J. Am. Chem. Soc. 1984, 106, 6097.
37. (a) Westwell, A. D.; Rayner, C. M. Tetrahedron: Asymmetry 1994, 5, 355.
38. (b) Westwell, A. D.; Thornton-Pett, M.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1995, 847.
39. (c) Marino, J. P.; Anna, L. J.; Fernández-de la Pradilla, R.; Martínez, M. V.; Montero, C.; Viso, A. Tetrahedron Lett. 1996, 37, 8031.
40. Koul, S.; Crout, D. H. G.; Errington, W. Tax, J. J. Chem. Soc., Perkin Trans. 1 1995, 2969.
41. Guerrero de la Rosa, V.; Ordóñez, M.; Alcudia, F.; Llera, J. M. Tetrahedron Lett. 1995, 36, 4889.
42. Results not published.
43. (a) Ferraboschi, P.; Pecora, F.; Reza-Elahi, S.; Santaniello, E. Tetrahedron: Asymmetry 1999, 10, 2497.
44. (b) Tanaka, K.; Yasuda, M. Tetrahedron: Asymmetry 1998, 9, 3275.
45. (c) Cygler, M.; Grochulski, P.; Kazlauskas, R. J.; Scharg, J. D.; Bouthillier, F.; Rubin, B.; Berrequi, A. N.; Gupta, A. K. J Am. Chem. Soc. 1994, 116, 3180.
46. (d) Kazlauskas, R. J.; Werssfloch, A. N. E.; Rappoport, A. T.; Luccia, L. A. J. Org. Chem. 1991, 56, 2656.
47. (a) Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.
48. (b) Jacobs, H. K.; Mueller, B. H.; Galopan. A. S. Tetrahedron 1992, 48, 8891.
49. (c) Domínguez, E.; Carretero, J. C.; Fernádez-Mayoralas, A.; Conde, S. Tetrahedron Lett. 1991, 32, 5159.
50. (d) Burgess, K.; Henderson, I. Tetrahedron: Asymmetry 1990, 1, 57.
51. The use of molecular sieves in lipase-mediated resolutions of alcohols has been previously reported. See: (a) Burgess, K.; Jennings, L. D. J Am. Chem. Soc. 1990, 112, 7434. (b) Ref. 15c.
52. The use of molecular sieves in lipase-mediated resolutions of alcohols has been previously reported. See: (a) Burgess, K.; Jennings, L. D. J Am. Chem. Soc. 1990, 112, 7434. (b) Ref. 15c.
53. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J Am. Chem. Soc. 1982, 104, 7294.
54. Kang, S.-K.; Park, Y.-W.; Kin, S.-G.; Jeon, J.-H. J. Chem. Soc., Perkin Trans. 1 1992, 405.
55. Similar results were observed in lipase-mediated acetylation reaction of (E)-4,4-dimethyl-1-(phenylsulfonyl)-1-penten-3-ol, Ref. 15a.
56. Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287.
57. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
58. Brown, H. C. Organic Synthesis via Boranes; John Wiley & Sons: New York, 1975; p. 256.
59. Juaristi, E.; Martínez-Richa, A.; García-Rivera, A.; Cruz-Sánchez, S. J. Org. Chem. 1983, 48, 2603.
60. Guerrero de la Rosa, V.; Ordóñez, M.; Llera, J. M.; Alcudia, F. Synthesis 1995, 761.
61. Kunieda, N.; Nokami, J.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1976, 49, 256.