Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles

Tetrahedron Asymmetry

Volumn 13, Issue 18, 2002, Pages 2039-2051

  Kamal, Ahmed ^a   Khanna, G B Ramesh ^a   Ramu, R ^a  

^a Division of Organic Chemistry   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3 CHLOROPHENYL) 3 HYDROXYPROPANENITRILE; 3 (4 CHLOROPHENYL) 3 HYDROXYPROPANENITRILE; 3 ACETYLOXY 3 (3 CHLOROPHENYL)PROPANENITRILE; 3 ACETYLOXY 3 (4 CHLOROPHENYL)PROPANENITRILE; 3 ACETYLOXY 3 (4 METHYLPHENYL)PROPANENITRILE; 3 ACETYLOXY 3 PHENYPROPANENITRILE; 3 HYDROXY 3 (4 METHYLPHENYL)PROPANENITRILE; 3 HYDROXY 3 PHENYLPROPANENITRILE; 3 PHENYL 3 (4 TRIFLUOROMETHYLPHENOXY) 1 PROPANAMINE; ACETIC ACID; ALCOHOL; ANTIDEPRESSANT AGENT; ATOMOXETINE; ETHER DERIVATIVE; FLUOXETINE; HEXANE; N METHYL 3 (2 METHOXYPHENOXY) 3 PHENYL 1 PROPANAMINE; N METHYL 3 (2 METHYLPHENOXY) 3 PHENYL 1 PROPANAMINE; N METHYL 3 PHENYL 3 (4 TRIFLUOROMETHYLPHENOXY) 1 PROPANAMINE; NISOXETINE; NITRILE; SODIUM CYANIDE; STYRENE OXIDE; TOLUENE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME IMMOBILIZATION; HYDROPHOBICITY; PRIORITY JOURNAL; TRANSESTERIFICATION;

EID: 0037145055     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00537-2     Document Type: Article

References (91)

1. Molloy, B. B.; Schmiegel, K. K. Ger. Pat. 2,500,110; US pat. 4,314,081 Klaus Florey. Analytical profiles of Drug Substances; Academic Press: San Diego, 1990; Vol. 19, pp. 193-219 and references cited therein.
2. Klieser E., Lehmann E., Heinrich K. Pharmacopsychiatry. 28:1995;14.
3. Wong D.T., Bymaster F.P., Engleman E.A. Life Sci. 57:1995;411.
4. Foster, B. J.; Lavangnino, E. R. EP 52,492; GB 2,087,883; JP 82,114,555.
5. Zerbe R.L., Rowe H., Enass G.G., Wong D., Farid N., Lemberger L. J. Pharmacol. Exp. Ther. 232:1985;139.
6. Chouinard G., Annable L., Brawejn J. Psychopharmacol. 83:1984;126.
7. Chouinard G., Annable L., Brawejn J., Labonte A., Jones B., Mercier P., Belanger M.C. Psychopharmacol. Bull. 21:1985;73.
8. Robertson D.W., Jones N.D., Swartzendruber J.K., Yang K.S., Wong D.T. J. Med. Chem. 31:1988;185.
9. Robertson D.W., Krushinski J.H., Fuller R.W., Leander J.D. J. Med. Chem. 31:1988;1412.
10. Piperaki S., Parissi-Poulou M. Chirality. 5:1993;258. and references cited therein.
11. Dittus, G. Methoden Der Organishen Chemie (Huben-Weyl); Muller, E., Ed.; Thieme Verlag: Stuggart, 1965; Vol. 6/3, p. 451 Henecka, H.; Erwin, O. (Huben-Weyl); Mothoden der Organishen chemie, 4th ed., Muller, E. Georg Thieme Verlag: Stuggart, 1952; Vol. 8, pp. 427-661.
12. Seidel W., Seebach D. Tetrahedron Lett. 23:1982;159.
13. Meyers A.I., Amos R.A. J. Am. Chem. Soc. 102:1980;870.
14. Ha D.C., Hart D.J. Tetrahedron Lett. 28:1987;4489.
15. Kramer A., Pfander H. Helv. Chim. Acta. 65:1982;293.
16. Amstutz R., Hungerbuhler E., Seebach D. Helv. Chim. Acta. 64:1981;1796.
17. Challis B.C., Challis J.A. Comprehensive Organic Chem. 2:1979;957 Pergamon Press, Oxford.
18. Simons S.S. Jr. J. Org. Chem. 38:1973;414.
19. Quiros M., Rebolledo F., Liz R., Gotor V. Tetrahedron: Asymmetry. 8:1997;3035.
20. Garcia M.J., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 3:1992;1519.
21. Garcia M.J., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 4:1993;2199.
22. Kumar A., Ner D.H., Dike S.Y. Tetrahedron Lett. 32:1991;1901.
23. Muller H.M., Seebach D. Angew. Chem., Int. Ed. Engl. 32:1993;477. and references cited therein.
24. Zhou B.N., Gopalan A.S., Van Middlesworth F., Shieh W.R., Sih C.J. J. Am. Chem. Soc. 105:1983;5925.
25. Boaz N.W. J. Org. Chem. 57:1992;4289.
26. Servi S. Synthesis. 1990;1. and references cited therein.
27. North M. Tetrahedron Lett. 37:1996;1699. and references cited therein.
28. Noyori R., Ohkuma T., Kitamura M., Takaya H., Sayo N., Kumobayashi H., Akutagawa S. J. Am. Chem. Soc. 109:1987;5856.
29. Soai K., Yamanoi T., Hikima H., Oyamada H. J. Chem. Soc., Chem. Commun. 1985;138. and references cited therein.
30. Mukaiyama T., Tomimori K., Oriyama T. Chem. Lett. 1985;813. and references cited therein.
31. Cohen S.G., Weinstein S.Y. J. Am. Chem. Soc. 86:1964;725.
32. Manzocchi A., Casati R., Fiecchi A., Santaniello E. J. Chem. Soc., Perkin Trans. 1. 1987;2753.
33. Masamune S., Sato T., Kim B.M., Wollmann T.A. J. Am. Chem. Soc. 108:1986;8279.
34. Ager D.J., Prakash I., Schaad D. Chem. Rev. 96:1996;835.
35. Enders D., Hartwig A., Raabe G., Runsink J. Angew. Chem., Int. Ed. Engl. 35:1996;2388.
36. Narasaka K., Pai F.-C. Tetrahedron. 40:1984;2233.
37. Evans D.A., Chapman K.T., Carreira M. J. Am. Chem. Soc. 110:1988;3560.
38. Haddad M., Dorbais J., Larcheveque M. Tetrahedron Lett. 38:1997;5981.
39. Narasaka K., Ukaji Y., Yamazaki S. Bull. Chem. Soc. Jpn. 59:1986;525.
40. Wang Y.-F., Izawa T., Kobayashi S., Ohno M. J. Am. Chem. Soc. 104:1982;6465.
41. Hashiguchi S., Kawada A., Natsugari H. J. Chem. Soc., Perkin Trans. 1. 1991;2435.
42. Hayashi Y., Rode J.J., Corey E.J. J. Am. Chem. Soc. 118:1996;5502.
43. Senanayake C.H., Fang K., Grover P., Bakale R.P., Vandenbossche C.P., Wald S.A. Tetrahedron Lett. 40:1999;819.
44. Genov M., Dimitrov V., Ivanova V. Tetrahedron: Asymmetry. 8:1997;3703.
45. Eliel E.L., He X.-C. J. Org. Chem. 55:1990;2114.
46. Kamal A., Khanna G.B.R. Tetrahedron: Asymmetry. 12:2001;405.
47. Kamal A., Ramana K.V., Rao M.V. J. Org. Chem. 66:2001;997.
48. Kamal A., Damayanthi Y., Reddy B.S.N., Laxminarayana B., Reddy B.S.P. Chem. Commun. 1997;1015.
49. Kamal A., Rao M.V. Tetrahedron: Asymmetry. 5:1994;1881.
50. Kamal A., Damayanthi Y., Rao M.V. Tetrahedron: Asymmetry. 3:1992;1361.
51. Smith J.G. Synthesis. 1984;629.
52. Nagata M., Okumura T. J. Chem. Soc., C. 17:1970;2365.
53. Chini M., Crotti P., Favero L., Macchia F. Tetrahedron Lett. 32:1991;4775.
54. Matsubara S., Onishi H., Utimoto K. Tetrahedron Lett. 31:1990;6209.
55. Mitchell D., Koening T.M. Tetrahedron Lett. 33:1992;3281.
56. Ohno H., Mori A., Inoue S. Chem. Lett. 1993;975.
57. Nagata W., Yoshioka M., Okumura T. Tetrahedron Lett. 1966;847.
58. Mullis J.C., Weber W.P. J. Org. Chem. 47:1982;2873.
59. Iranpoor N., Shekarriz M. Synth. Commun. 29:1999;2249.
60. Sassaman M.B., Prakash G.K.S., Olah G.A. J. Org. Chem. 55:1990;2016.
61. Vougioukas A.E., Kagan H.B. Tetrahedron Lett. 28:1987;5513.
62. Hayashi M., Tamura M., Oguni N. Synlett. 1992;663.
63. Imi K., Yanagihara N., Utimoto K. J. Org. Chem. 52:1987;1013.
64. Sugita K., Ohta A., Onaka M., Izumi Y. Chem. Lett. 3:1990;481.
65. Itoh T., Takagi Y., Fujisawa T. Tetrahedron Lett. 30:1989;3811.
66. Fuganti C., Pedrocchi-Fantoni G., Servi S. Tetrahedron Lett. 31:1990;4195.
67. Smallridge A.J., Ten A., Trewhella M.A. Tetrahedron Lett. 39:1998;5121.
68. Florey P., Smallridge A.J., Ten A., Trewhella M.A. Org. Lett. 1:1999;1879.
69. Dehli J.R., Gotor V. Tetrahedron: Asymmetry. 11:2000;3693.
70. Itoh T., Tagaki Y. Chem. Lett. 1989;1505.
71. Itoh T., Tagaki Y., Nishiyama S. J. Org. Chem. 56:1991;1521.
72. Itoh T., Hiyama Y., Betchaku A. Tetrahedron Lett. 34:1993;2617.
73. Itoh T., Tgaki Y., Murakami T., Hiyama Y., Tsukube H. J. Org. Chem. 61:1996;2158.
74. Garcia-Urdiales E., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 12:2001;3047.
75. Pamies O., Backvall J.-E. Adv. Synth. Catal. 343:2001;726.
76. Kamal, A.; Khanna, G. B. R.; Rao, M. V.; Raghavan, K. V. Indian Patent Application No. NF 329/00; PCT Application No. PCT/1NO1/00008.
77. Goa Y., Sharpless K.B. J. Org. Chem. 53:1988;4081.
78. Mitchell D., Koenig T.M. Synth. Commun. 25:1995;1231.
79. Schneider M.P., Goergens U. Tetrahedron: Asymmetry. 3:1992;525.
80. Raju S.B., Chiou T.-W., Tai D.-F. Tetrahedron: Asymmetry. 6:1995;1519.
81. Liu H.-L., Hoff B.H., Anthosen T. J. Chem. Soc., Perkin Trans. 1. 2000;1767.
82. Srebnik M., Ramchandran P.V., Brown H.C. J. Org. Chem. 53:1988;2916.
83. Corey E.J., Reichard G.A. Tetrahedron Lett. 30:1989;5207.
84. Fronza G., Fuganti C., Grasselli P., Mele A. J. Org. Chem. 56:1991;6019.
85. Kumar A., Ner D.H., Dike S.Y. Tetrahedron Lett. 32:1991;1901.
86. Chenevert R., Fortier G. Chem. Lett. 1991;1603.
87. Chenevert R., Fortier G., Rhlid R.B. Tetrahedron. 48:1992;6769.
88. Huang H.-L., Liu L.T., Chen S.-F., Ku H. Tetrahedron: Asymmetry. 9:1998;1637.
89. Master H.E., Newadkar R.V., Rane R.A., Kumar A. Tetrahedron Lett. 37:1996;9253.
90. Bracher F., Litz T. Bioorg. Med. Chem. 4:1996;877.
91. Brown H.C., Choi Y.M., Narasimhan S. J. Org. Chem. 47:1982;3153.