Lipase-catalyzed transesterification of 2-hydroxy-2- (pentafluorophenyl)acetonitrile leading to (1R,2R)-and (1S,2S)-bis (pentafluorophenyl)ethane-1,2-diol

Journal of Organic Chemistry

Volumn 65, Issue 9, 2000, Pages 2740-2747

  Sakai, Takashi ^a   Miki, Yasushi ^a   Tsuboi, Masashi ^a   Takeuchi, Hiroaki ^a   Ema, Tadashi ^a   Uneyama, Kenji ^a   Utaka, Masanori ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACETONITRILE DERIVATIVE; CYANOHYDRIN; NAPHTHALENE DERIVATIVE; PERFLUORO COMPOUND; PHENYL GROUP; TRIACYLGLYCEROL LIPASE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; ESTERIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034608029     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9918551     Document Type: Article

References (56)

1. (a) Wang, Z.-M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302-8303 and references therein.
2. (b) Frost, C. G.; Williams, M. J. Synlett 1994, 551-552.
3. (c) Bruin, M. E.; Kündig, E. P. Chem. Commun. 1998, 2635-2636.
4. (d) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1219-1223.
5. (e) Shindo, M.; Koga, K.; Tomioka, K. J. Org. Chem. 1998, 63, 9351-9357 and references therein.
6. (f) For lipase-catalyzed desymmetrization of the meso-1,2-diphenylethane-1,2-diol: Nicolosi, G.; Patti, A.; Piattelli, M.; Sanfilippo, C. Tetrahedron: Asymmetry 1994, 5, 283-288.
7. (a) Stolle, A.; Becker, H.; Salaün, J.; Meijere, A. Tetrahedron Lett. 1994, 35, 3521-3524.
8. (b) Marshall, J. A.; Xie, S. J. Org. Chem. 1995, 60, 7230-7237.
9. (c) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2113-2116.
10. (d) Fujioka, H.; Matsunaga, N.; Kitagawa, H.; Nagatomi, Y.; Kondo, M.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2117-2120.
11. (e) Cossy, J.; Bouzbouz, S. Tetrahedron Lett. 1996, 37, 5091-5094.
12. (f) Akhoon, K. M.; Myles, D. C. J. Org. Chem. 1997, 62, 6041-6045.
13. (g) Tunge, J. A.; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc: 1999, 121, 4520-4521.
14. Filler, R. In Fluorine-Containing Molecules: Structure, Reactivity, Synthesis, and Applications; Liebman, J. F., Greenberg, A., Dolbier, W. R., Jr., Eds.; VCH: Weinheim, 1988; pp 19-41.
15. Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598.
16. (a) Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquini, M.; Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1019-1020.
17. (b) Laatikainen, R.; Ratilainen, J.; Sebastian, R.; Santa, H. J. Am. Chem. Soc. 1995, 117, 11006-11010.
18. (a) Hernádez-Trujillo, J.; Costas, M. J. Chem. Soc., Faraday Trans. 1993, 89, 2441-2443.
19. (b) Hunter, C. A.; Lu, X.-J.; Kapteijn, G. M.; van Koten, G. J. Chem. Soc., Faraday Trans. 1995, 91, 2009-2015.
20. (c) Williams, V. E.; Lemieux, R. P.; Thatcher, G. R. J. J. Org. Chem. 1996, 61, 1927-1933.
21. Recently, an example for charge-transfer interaction between hexafluorobenzene and metallocene has been reported: Aspley, C. J.; Boxwell, C.; Buil, M. L.; Higgitt, C. L.; Long, C.; Perutz, R. N. Chem. Commun. 1999, 1027-1028.
22. (a) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 248-251.
23. (b) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641-3649.
24. Fujita, M.; Nagao, S.; Iida, M.; Ogata, K.; Ogura, K. J. Am. Chem. Soc. 1993, 115, 1574-1576.
25. (a) Gillard, R. E.; Stoddart, J. F.; White, A. J. P.; Williams, B. J.; Williams, D. J. J. Org. Chem. 1996, 61, 4504-4505.
26. (b) Li, Z.-T.; Becher, J. Synlett 1997, 557-560.
27. (c) Ballardini, R.; Balzani, V.; Credi, A.; Brown, C. L.; Gillard, R. E.; Montalti, M. Philp, D.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, B. J.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 12503-12513.
28. Doyon, J. B.; Jain, A. Org. Lett. 1999, 1, 183-185.
29. (a) Ishihara, K.; Hanaki. N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721-1730.
30. (b) Ishihara, K.; Kurihara, H.; Yamamoto, H. Synlett 1997, 597-599.
31. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 5664-5665.
32. Parks, D. J.; Piers, W. E., J. Am. Chem. Soc. 1996, 118, 9440-9441.
33. Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327-5328.
34. (a) Kan, T.; Ohfune, Y. Tetrahedron Lett. 1995, 36, 943-946.
35. (b) Jacques, F.; Dupeyroux, H.; Joly, J.-P.; Chapleur, Y. Tetrahedron Lett. 1997, 38, 73-76.
36. Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; de Alaniz, J. R. Tetrahedron Lett. 1998, 39, 8791-8794.
37. (a) Ojima, I.; Kwon, H. B. J. Am. Chem. Soc. 1988, 110, 5617-5621.
38. (b) Kündig, E. P.; Dupré, C.; Bourdin, B.; Cunningham, A., Jr.; Pons, D. Helv. Chem. Acta 1994, 77, 421-428.
39. (c) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571-2574.
40. (a) Sakai, T.; Kubo, K.; Kashino, S.; Uneyama, K. Tetrahedron: Asymmetry 1996, 7, 1883-1886.
41. (b) Sakai, T.; Takayama, T.; Ohkawa, T.; Yoshio, O.; Ema, T.; Utaka, M. Tetrahedron Lett. 1997, 38, 1987-1991.
42. (c) Sakai, T.; Miki, Y.; Nakatani, M.; Ema, T.; Uneyama, K.; Utaka, M. Tetrahedron Lett. 1998, 39, 5233-5236.
43. Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353-3361.
44. Gassman, P. G.; Talley, J. J. Tetrahedron Lett. 1978, 25, 3773-3776.
45. Conventional method for nonfluorinated analogue using acetonecyanohydrin was not applicable for (±)-2. Inagaki, M.; Hatanaka, A.; Mimura, M.; Hiratake, J.; Nishioka, T.; Oda, J. Bull. Chem. Soc. Jpn. 1992, 65, 111-120.
46. Toyonite-DM, a new type of the spherical ceramics support having 155 ± 5 μm average diameter, was supplied by Toyo Denka Kogyo Co., Ltd., Kochi, Japan. The porous ceramics is prepared from kaolin minerals and the average pore size is nearly 100 nm. The pores have cross linkages consisting of methacryloxy groups at the end of methylene chains for binding lipases. The immobilized lipases on this support usually greatly accelerate the reaction rate. Yamashita, Y.; Kamori, M.; Takeneka, H.; Takahashi, J. Jpn Kokai Tokkyo Koho 09 313 179, 1997; Chem. Abstr. 1998, 128, 72373.
47. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
48. We have reported the low-temperature effect for enhancement of enantioselectivity in lipase-catalyzed transesterifications of both primary and secondary alcohols: (a) Sakai, T.; Kawabata, I.; Kishimoto, T.; Ema, T.; Utaka, M. J. Org. Chem. 1997, 62, 4906-4907. (b) Sakai, T.; Kishimoto, T.; Tanaka, Y.; Ema, T.; Utaka, M. Tetrahedron Lett. 1988, 39, 7881-7884.
49. We have reported the low-temperature effect for enhancement of enantioselectivity in lipase-catalyzed transesterifications of both primary and secondary alcohols: (a) Sakai, T.; Kawabata, I.; Kishimoto, T.; Ema, T.; Utaka, M. J. Org. Chem. 1997, 62, 4906-4907. (b) Sakai, T.; Kishimoto, T.; Tanaka, Y.; Ema, T.; Utaka, M. Tetrahedron Lett. 1988, 39, 7881-7884.
50. Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665.
51. Recently, intermolecular F⋯H interaction between perfluoroarene- and arene-containing molecules has been reported: (a) Thalladi, V. R.; Weiss, H.-C.; Bläser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 8702-8710. (b) Renak, M. L.; Bartholomew, G. P.; Wang, S.; Ricatto, P. J.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121, 7787-7799.
52. Recently, intermolecular F⋯H interaction between perfluoroarene- and arene-containing molecules has been reported: (a) Thalladi, V. R.; Weiss, H.-C.; Bläser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 8702-8710. (b) Renak, M. L.; Bartholomew, G. P.; Wang, S.; Ricatto, P. J.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121, 7787-7799.
53. Brussee, J.; Roos, E. C.; van der Gen, A. Tetrahedron Lett. 1988, 29, 4485-4488.
54. Addition of excess acetyl chloride directly to residual cyanohydrin 2 was unsuccessful, and thus one repetition procedure was usually required.
55. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
56. Büyüktimkin, N.; Buschauer, A. J. Chromatogr. 1988, 450, 281-283.