Resolution of racemic 1-azido-3-aryloxy-2-propanols by lipase-catalyzed enantioselective acetylation

Tetrahedron Asymmetry

Volumn 11, Issue 13, 2000, Pages 2719-2732

  Pchelka, Beata Krystyna ^a,b   Loupy, André ^a   Plenkiewicz, Jan ^b   Blanco, Luis ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 AZIDO 3 ARYLOXY 2 PROPANOL; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; BACTERIAL ENZYME; FUNGAL ENZYME; ISOPROPENYL ACETATE; SOLVENT; TOLUENE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA; CANDIDA RUGOSA; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; ESTERIFICATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS FLUORESCENS; RACEMIC MIXTURE; STEREOCHEMISTRY; TECHNIQUE; TEMPERATURE;

EID: 0034647968     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00229-9     Document Type: Article

References (96)

1. (a) Pchelka, B. K.; Radomska, J.; Plenkiewicz, J. Synthetic Commun. 1998, 28, 4355.
2. (b) Pchelka, B. K.; Gelo-Pujic, M.; Guibé-Jampel, E. J. Chem. Soc., Perkin Trans. 1 1998, 2625.
3. (c) Barnier, J. P.; Morisson, V.; Volle, I.; Blanco, L. Tetrahedron: Asymmetry 1999, 10, 1107.
4. Besse, P.; Veschambre, H.; Chênevert, R.; Dickman, M. Tetrahedron: Asymmetry 1994, 5, 1727.
5. Powell, J. R.; Wainer, I. W.; Drayer, D. E. Drug Stereochemistry Analytical Methods and Pharmacology; Marcel Dekker, 1988.
6. The Merck Index, 11th ed., 1989.
7. (a) Howe, R.; Shanks, R. G. Nature 1966, 1336.
8. (b) Jamali, F.; Mehvar, R.; Pasutto, F. M. J. Pharm. Sci. 1989, 78, 695.
9. (c) Nelson, W. L.; Burke, T. R. J. Org. Chem. 1978, 43, 3641.
10. (d) Howe, R.; Rao, B. S. J. Med. Chem. 1968, 11, 1118.
11. (a) Bevinakatti, H. S.; Banerji, A. A. J. Org. Chem. 1992, 57, 6003.
12. (b) Shieh, W. R.; Gou, D. M.; Chen, C. S. J. Chem. Soc., Chem. Commun. 1991, 651.
13. (c) Terao, Y.; Murata, M.; Achiwa, K.; Nishino, T.; Akamatsu, M.; Kamimura, M. Tetrahedron Lett. 1988, 29, 5173.
14. (d) Wang, Y. F.; Chen, S. T.; Liu, K. K. C.; Wong, C. H. Tetrahedron Lett. 1989, 30, 1917.
15. (e) Wünsche, K.; Schwaneberg, U.; Bornscheuer, U. T.; Meyer, H. H. Tetrahedron: Asymmetry 1996, 7, 2017.
16. (a) Deyrup, J. A. The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; John Wiley & Sons: New York, 1993; Vol. 42, Part 1, p. 1.
17. (b) Duggan, M. E.; Karanewsky, D. S. Tetrahedron Lett. 1983, 24, 2935.
18. (c) Laurent, A.; Mison, P.; Nafti, A.; Cheikh, R. B.; Chaabouni, R. J. Chem. Res. 1984, 354.
19. (d) Tsuge, O.; Kanemasa, S.; Suga, H.; Matsuda, K. Heterocycles 1984, 22, 1955.
20. (a) Tomasz, M.; Jung, M.; Verdine, G.; Nakanishi, K. J. Am. Chem. Soc. 1984, 106, 7367.
21. (b) Danishefsky, S.; Ciufolini, M. J. Am. Chem. Soc. 1984, 106, 6424.
22. (a) Bardos, T. J.; Ambrus, J. L.; Ambrus, C. M. J. Surg. Oncol. 1971, 3, 431.
23. (b) Wampler, G. L.; Kuperminc, M.; Regelson, W. Cancer Chemother. Pharmacol. 1980, 4, 49.
24. (c) Belgrad, R.; Wampler, G. L. Int. J. Radiat. Oncol. Biol. Phys. 1982, 8, 1219.
25. (d) Perlman, M. E.; Bardos, T. J. J. Org. Chem. 1988, 53, 1761.
26. Leo, A.; Müller, M. Eur. Patent 94 595, 1983; Chem. Abstr. 1984, 100, P 120862n.
27. Leo, A.; Müller, M. Eur. Patent 94 595, 1983; Chem. Abstr. 1984, 100, P 120862n.
28. Lalka, D.; Bardos, T. J. Biochem. Pharmacol. 1975, 24, 455.
29. (a) Nobuhide, Y.; Kazuo, A.; Kobunshi Ronbunshu 1982, 39, 507; Chem. Abstr. 1983, 98, 4837z.
30. (a) Nobuhide, Y.; Kazuo, A.; Kobunshi Ronbunshu 1982, 39, 507; Chem. Abstr. 1983, 98, 4837z.
31. (b) Nobuhide, Y.; Shigekazu, I. Nippon Kagaku kaishi 1986, 96; Chem. Abstr. 1986, 105, 190600c.
32. (b) Nobuhide, Y.; Shigekazu, I. Nippon Kagaku kaishi 1986, 96; Chem. Abstr. 1986, 105, 190600c.
33. Sommerdijk, N. A. J. M.; Buynsters, P. J. J. A.; Akdemir, H.; Geurts, D. G.; Nolte, R. J. M.; Zwanenburg, B. J. Org. Chem., 1997, 62, 4956.
34. (a) Guy, A.; Doussot, J.; Garreau, R.; Godefroy-Falguières, A. Tetrahedron: Asymmetry 1992, 3, 247.
35. (b) Kamal, A.; Arifuddin, M.; Rao, M. V. Tetrahedron: Asymmetry 1999, 10, 4261.
36. (c) Sutowardoyo, K. I.; Emziane, M.; Lhoste, P.; Sinou, D. Tetrahedron 1991, 47, 1435.
37. (d) Emziane, M.; Lhoste, P.; Sinou, D. Synthesis 1988, 541.
38. (e) Sutowardoyo, K. I.; Sinou, D. Tetrahedron: Asymmetry 1991, 2, 437.
39. Lohray, B. B.; Gao, Y.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623.
40. Lohray, B. B.; Ahuja, J. R. J. Chem. Soc., Chem. Commun. 1991, 95.
41. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810.
42. Mischitz, M.; Faber, K. Tetrahedron Lett. 1994, 35, 81.
43. (a) Besse, P.; Veschambre, H. Tetrahedron: Asymmetry 1993, 4, 1271.
44. (b) Besse, P.; Veschambre, H.; Dickman, M.; Chênevert, R. J. Org. Chem. 1994, 59, 8288.
45. Faber, K.; Hönig, H.; Seufer-Wasserthal, P. Tetrahedron Lett. 1988, 29, 1903.
46. Foelsche, E.; Hickel, A.; Hönig, H.; Seufer-Wasserthal, P. J. Org. Chem., 1990, 55, 1749.
47. Pederson, R. L.; Liu, K. K. C.; Rutan, J. F.; Chen, L.; Wong, C. H. J. Org. Chem. 1990, 55, 4897.
48. Ader, U.; Schneider, M. P. Tetrahedron: Asymmetry 1992, 3, 205.
49. Theil, F.; Lemke, K.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1323.
50. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
51. Pchelka, B. K.; Plenkiewicz, J. Org. Prep. Proc. Int. 1998, 30, 87.
52. (a) Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
53. (b) Guo, Z. W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6836.
54. (a) Anthonsen, T.; Jongejan, J. A. Meth. Enzymol. 1997, 286, 473.
55. (b) Anthonsen, T.; Hoff, B. H. Chem. Phys. Lipids 1998, 93, 199.
56. (a) Faber, K. Biotransformations in Organic Media, 3rd ed.; Springer: Graz, Austria, 1996.
57. (b) Kvittingen, L. Tetrahedron 1994, 50, 8253.
58. (c) Rubio, E.; Alfonso, F. M.; Klibanov, A. M. J. Am. Chem. Soc. 1991, 113, 695.
59. Fitzpatrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1991, 113, 3166.
60. Erna, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymmetry 1996, 7, 625.
61. (a) Weber, H. K.; Zuegg, J.; Faber, K.; Pleiss, J. J. Mol. Catal. B: Enzymatic 1997, 3, 131.
62. (b) Weber, H. K.; Stecher, H.; Faber, K. Biotechnol. Lett. 1995, 17, 803.
63. (c) Faber, K.; Riva, S. Synthesis 1992, 895.
64. Sakai, T.; Kawabata, I.; Kishimoto, T.; Ema, T.; Utaka, M. J. Org. Chem. 1997, 62, 4906.
65. (a) Lam, L. K. P.; Hui, R. A. H. F.; Jones, J. B. J. Org. Chem. 1986, 51, 2047.
66. (b) Yasufuku, Y.; Ueji, S. Biotechnol. Lett. 1995, 17, 1311.
67. (c) Koskinen, A. M. P.; Klibanov, A. M. Enzymatic Reactions in Organic Media; Blackie Academic, Eds.: Glasgow, 1996.
68. (d) Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366.
69. (e) Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799.
70. (f) Zaks, A.; Klibanov, A. M. Science 1984, 224, 1249.
71. (g) Adams, M. W. W.; Kelly, R. M.; Biocatalysis at extreme temperatures. ACS Symp. Ser. 1992, 498.
72. (a) Adams, M. W. W; Kelly, R. M. Chem. Eng. News 18 Dec. 1995, 32.
73. ® SP 435, product sheet from Enzyme Process Division, Novo-Nordisk, Bagsvaerd, Denmark.
74. Phillips, R. S. Trends Biotechnol. 1996, 14, 13 and quoted references.
75. (a) Kermasha, S.; Bisakowski, B.; Ramaswamay, H.; Vandevoort, F. Int. J. Food Sci. Technol. 1993, 28, 617.
76. (b) Orlando, A. R.; Mossa, G.; Dinzeo, G. Bioelectromagnetics 1994, 15, 303.
77. (c) Ponne, C. T.; Meijer, M. M. T.; Bartels, P. V. J. Agr. Food Chem. 1994, 42, 2583.
78. (d) Stavinoha, W. B. Scanning 1993, 15, 115.
79. (a) Porcelli, M.; Cacciapuoti, G.; Fusco, S.; Massa, R.; Ambrosio, G.; Bertoldo, C.; De Dosa, M.; Zappia, V. FEBS Lett. 1997, 402, 102, and references cited therein.
80. (b) Kabza, K. G.; Gestwicki, J. E.; McGrath, J. L.; Petrassi, H. M. J. Org. Chem. 1996, 61, 9599.
81. (a) Deshayes S.; Liagre, M.; Loupy, A.; Luche, J. L.; Petit, A. Tetrahedron 1999, 55, 10851, and references cited therein.
82. (b) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathé, D. Synthesis 1998, 1213, and references cited therein.
83. Carrillo-Munoz, J. R.; Bouvet, D.; Guibé-Jampel, E.; Loupy, A.; Petit, A. J. Org. Chem. 1996, 61, 7746.
84. Gelo-Pujic, M.; Guibé-Jampel, E.; Loupy, A.; Galema, S. A.; Mathé, D. J. Chem. Soc., Perkin Trans. 1 1996, 2777.
85. Gelo-Pujic, M.; Guibé-Jampel, E.; Loupy, A.; Trincone, A. J. Chem. Soc., Perkin Trans. 1 1997, 1001.
86. Parker, M. C.; Besson, T.; Lamare, S.; Legoy, M. D. Tetrahedron Lett. 1996, 37, 8383.
87. Lin, G.; Lin, W. Y. Tetrahedron Lett. 1998, 39, 4333.
88. (a) Theil, F.; Schick, H. Synthesis 1991, 533.
89. (b) Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101.
90. (c) Konno, H.; Ogasawara, K. Synthesis 1999, 1135.
91. (d) Yoshida, N.; Konno, H.; Kamikubo, T.; Takahashi, M.; Ogasawara, K. Tetrahedron: Asymmetry 1999, 10, 3849.
92. Broos, J.; Sakodinskaya, I. K.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 255.
93. (a) Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617.
94. (b) Itoh, T.; Takagi, Y.; Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61, 2158.
95. (a) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991.
96. (b) Takagi, Y.; Ino, R.; Kihara, H.; Itoh, T.; Tsukube, H. Chem. Lett. 1997, 1247.