Nitrile biotransformations for the synthesis of enantiomerically enriched β2-, and β3-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity

Tetrahedron Asymmetry

Volumn 19, Issue 3, 2008, Pages 322-329

  Ma, Da You ^a   Wang, De Xian ^a   Pan, Jie ^a   Huang, Zhi Tang ^a   Wang, Mei Xiang ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 ALLYLOXYMETHYL 3 PHENYLPROPIONAMIDE; 2 ALLYLOXYMETHYL 3 PHENYLPROPIONIC ACID; 2 BENZYLOXYMETHYL 3 PHENYLPROPIONAMIDE; 2 BENZYLOXYMETHYL 3 PHENYLPROPIONITRILE; 2 HYDROXYMETHYL 3 PHENYLPROPIONAMIDE; 2 HYDROXYMETHYL 3 PHENYLPROPIONIC ACID; 2 HYDROXYMETHYL 3 PHENYLPROPIONITRILE; 2 METHOXYMETHYL 3 PHENYLPROPIONAMIDE; 2 METHOXYMETHYL 3 PHENYLPROPIONIC ACID; 2 METHOXYMETHYL 3 PHENYLPROPIONITRILE; 3 ALLYLOXY 3 PHENYLPROPIONAMIDE; 3 ALLYLOXY 3 PHENYLPROPIONIC ACID; 3 ALLYLOXY 3 PHENYLPROPIONITRILE; 3 BENZYLOXY 3 PHENYLPROPIONAMIDE; 3 BENZYLOXY 3 PHENYLPROPIONITRILE; 3 HYDROXY 3 PHENYLPROPIONAMIDE; 3 HYDROXY 3 PHENYLPROPIONITRILE; 3 METHOXY 3 PHENYLPROPIONAMIDE; 3 METHOXY 3 PHENYLPROPIONIC ACID; 3 METHOXY 3 PHENYLPROPIONITRILE; 3 PHENYL 2 (TRIMETHYLSILYL METHYL)PROPIONITRILE; 3 PHENYLHYDRACRYLIC ACID; NITRILE; PROPIONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; BIOTRANSFORMATION; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; ISOMER; METHYLATION; PRIORITY JOURNAL;

EID: 39149089631     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.01.017     Document Type: Article

References (82)

1. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), John Wiley & Sons pp 56-82
2. For recent examples, see:. Li K.W., Wu J., Xing W., and Simon J.A. J. Am. Chem. Soc. 118 (1996) 7237
3. Labeeuw O., Blanc D., Phansavath P., Ratovelomanana-Vidal V., and Genet J.-P. Eur. J. Org. Chem. (2004) 2352
4. Herb C., Bayer A., and Maier M.E. Chem. Eur. J. 10 (2004) 5649
5. Kamal A., Khanna G.B.R., and Ramu R. Tetrahedron: Asymmetry 13 (2002) 2039
6. Genet J.-P. Acc. Chem. Res. 36 (2003) 908
7. Hagemann B., Junge K., Enthaler S., Michalik M., Riermeier T., Monsees A., and Beller M. Adv. Synth. Catal. 347 (2005) 1978
8. Touati R., Gmiza T., Jeulin S., Deport C., Ratovelomanana-Vidal V., Hassine B.B., and Genet J.-P. Synlett (2005) 2478
9. Wang Z., Zhao C., Pierce M.E.J., and Fortunak M. Tetrahedron: Asymmetry 10 (1999) 225
10. For a review, see:. Nelson S.G. Tetrahedron: Asymmetry 9 (1998) 357
11. For recent important examples, see:. Denmark S.E., Beutner G.L., Wynn T., and Eastgate M.D. J. Am. Chem. Soc. 127 (2005) 3774
12. Denmark S.E., Fan Y., and Eastgate M.D. J. Org. Chem. 70 (2005) 5235
13. Yamashita Y., Ishitani H., Shimizu H., and Kobayashi S. J. Am. Chem. Soc. 124 (2002) 3292
14. For recent reviews, see:. Ocampo R., and Dolbier W.R. Tetrahedron 60 (2004) 9325
15. Ribeiro C.M.R., and Farias F.M.C. Mini-Rev. Org. Chem. 3 (2006) 1
16. Nakamura K., Kawai Y., Nakajima N., and Ohno A. J. Org. Chem. 56 (1991) 4778 and the references cited therein
17. For recent examples, see:. Ribeiro J.B., Ramos M.d.C.K.V., Neto F.R.d.A., Leite S.G.F., and Antunes O.A.C. J. Mol. Catal. B: Enzym. 24-25 (2003) 121
18. Vitinius U., Schaffner K., and Demuth M. J. Photochem. Photobiol. A: Chem. 169 (2005) 197
19. Rodriguez S., Kayser M.M., and Stewart J.D. J. Am.Chem. Soc. 123 (2001) 1547
20. Wilson W.K., Baca S.B., Barber Y.J., Scallen T.J., and Morrow C.J. J. Org. Chem. 48 (1983) 3960
21. Boaz N.W. J. Org. Chem. 57 (1992) 4289
22. Itoh T., Fakagi Y., and Nishigama S. J. Org. Chem. 56 (1991) 1521
23. Feichter C., Faber K., and Griengl H. Tetrahedron Lett. 30 (1989) 551
24. Kumar S., Padhi S.K., and Chadha A. Tetrahedron: Asymmetry 16 (2005) 2790
25. Padhi S.K., Pandian N.G., and Chadha A. J. Mol. Catal. B: Enzym. 29 (2004) 25
26. For overviews, see:. Kobayashi M., and Shimizu S. FEMS Microbiol. Lett. 120 (1994) 217
27. Meth-Cohn O., and Wang M.-X. J. Chem. Soc., Perkin Trans. 1 (1997) 1099
28. Meth-Cohn O., and Wang M.-X. J. Chem. Soc., Perkin Trans. 1 (1997) 3197 and references cited therein
29. Nagasawa T., Schimizu H., and Yamada H. Appl. Microbiol. Biotechnol. 40 (1993) 189
30. For reviews, see:. Sugai T., Yamazaki T., Yokoyama M., and Ohta H. Biosci. Biotech. Biochem. 61 (1997) 1419
31. Martinkova L., and Kren V. Biocatal. Biotransform. 20 (2002) 73
32. Wang M.-X. Top. Catal. 35 (2005) 117
33. For recent examples, see:. DeSantis G., Zhu Z., Greenberg W.A., Wong K., Chaplin J., Hanson S.R., Farwell B., Nicholson L.W., Rand C.L., Weiner D.P., Robertson D.E., and Burk M.J. J. Am. Chem. Soc. 124 (2002) 9024
34. Wu Z.-L., and Li Z.-Y. Chem. Commun. (2003) 386
35. Effenberger F., and Oßwald S. Tetrahedron: Asymmetry 12 (2001) 279
36. Hann E.C., Sigmund A.E., Fager S.K., Cooling F.B., Gavagan J.E., Ben-Bassat A., Chauhan S., Payne M.S., Hennessey S.M., and DiCosimo R. Adv. Synth. Catal. 345 (2003) 775
37. Wu Z.-L., and Li Z.-Y. J. Mol. Catal. B: Enzym. 22 (2003) 105
38. Preiml M., Hillmayer K., and Klempier N. Tetrahedron Lett. 44 (2003) 5057
39. Yokoyama M., Kashiwagi M., Iwasaki M., Fushuku K., Ohta H., and Sugai T. Tetrahedron: Asymmetry 15 (2004) 2817
40. Blakey A.J., Colby J., Williams E., and O'Reilly C. FEMS Microbiol. Lett. 129 (1995) 57
41. Colby J., Snell D., and Black G.W. Monatsh. Chem. 131 (2000) 655
42. O'Mahony R., Doran J., Coffey L., Cahill O.J., Black G.W., and O'Reilly C. Antonie van Leeuwenhoek 87 (2005) 221
43. Wang M.-X., Lu G., Ji G.-J., Huang Z.-T., Meth-Cohn O., and Colby J. Tetrahedron: Asymmetry 11 (2000) 1123
44. Wang M.-X., Li J.-J., Ji G.-J., and Li J.-S. J. Mol. Catal. B: Enzym. 14 (2001) 77
45. Wang M.-X., and Zhao S.-M. Tetrahedron Lett. 43 (2002) 6617
46. Wang M.-X., and Zhao S.-M. Tetrahedron: Asymmetry 13 (2002) 1695
47. Gao M., Wang D.-X., Zheng Q.-Y., Huang Z.-T., and Wang M.-X. J. Org. Chem. 72 (2007) 6060
48. Wang M.-X., and Lin S.-J. Tetrahedron Lett. 42 (2001) 6925
49. Wang M.-X., and Lin S.-J. J. Org. Chem. 67 (2002) 6542
50. Wang M.-X., Lin S.-J., Liu J., and Zheng Q.-Y. Adv. Synth. Catal. 346 (2004) 439
51. Wang M.-X., Liu J., Wang D.-X., and Zheng Q.-Y. Tetrahedron: Asymmetry 16 (2005) 2409
52. Wang M.-X., and Feng G.-Q. Tetrahedron Lett. 41 (2000) 6501
53. Wang M.-X., and Feng G.-Q. New J. Chem. (2002) 1575
54. Wang M.-X., and Feng G.-Q. J. Org. Chem. 68 (2003) 621
55. Wang M.-X., and Feng G.-Q. J. Mol. Catal. B: Enzym. 18 (2002) 267
56. Wang M.-X., Feng G.-Q., and Zheng Q.-Y. Adv. Synth. Catal. 345 (2003) 695
57. Wang M.-X., Feng G.-Q., and Zheng Q.-Y. Tetrahedron: Asymmetry 15 (2004) 347
58. Feng G.-G., Wang D.-X., Zheng Q.-Y., and Wang M.-X. Tetrahedron: Asymmetry 17 (2006) 2775
59. Wang M.-X., Lin S.-J., Liu C.-S., Zheng Q.-Y., and Li J.-S. J. Org. Chem. 68 (2003) 4570
60. Wang M.-X., Deng G., Wang D.-X., and Zheng Q.-Y. J. Org. Chem. 70 (2005) 2439
61. Wang J.-Y., Wang D.-X., Zheng Q.-Y., Huang Z.-T., and Wang M.-X. J. Org. Chem. 72 (2007) 2040
62. Wang J.-Y., Wang D.-X., Pan J., Huang Z.-T., and Wang M.-X. J. Org. Chem. 72 (2007) 9391
63. Gao M., Wang D.-X., Zheng Q.-Y., and Wang M.-X. J. Org. Chem. 71 (2006) 9532
64. Ma D.-Y., Zheng Q.-Y., Wang D.-X., and Wang M.-X. Org. Lett. 8 (2006) 15 3231
65. Yokoyama M., Imai N., Sugai T., and Ohta H. J. Mol. Catal. B: Enzym. 1 (1996) 135
66. Wang M.X., and Wu Y. Org. Biomol. Chem. 1 (2003) 535
67. Wang M.-X., and Zhao S.-M. Chin. J. Chem. 20 (2002) 1297
68. Wu Z.-L., and Li Z.-Y. J. Mol. Catal. B: Enzym. 22 (2003) 105
69. Martínková L., Klempier N., Bardakji J., Kandelbauer A., Ovesná M., Podařilová T., Kuzma M., Přepechalová I., Griengl H., and Kren V. J. Mol. Catal. B: Enzym. 14 (2001) 95
70. Cosp A., Romea P., Urpi F., and Vilarrasa J. Tetrahedron Lett. 42 (2001) 4629 We thank Dr. Romea, P. and Dr. Urpi, F. at University of Barcelona for providing the specific optical rotatory power of (S)-3-Methoxy-3-phenylpropionic acid
71. Chen C.-S., Fujimoto Y., Girdaukas G., and Sih C.J. J. Am. Chem. Soc. 104 (1982) 7294
72. Program 'Selectivity' by Faber, K.; Hoenig, H. http://www.cis.TUGraz.at/orgc/.
73. Wang M.-X., Liu C.-S., Li J.-S., and Meth-Cohn O. Tetrahedron Lett. 41 (2000) 8549
74. Wang M.-X., Liu C.-S., and Li J.-S. Tetrahedron: Asymmetry 12 (2001) 3367
75. Jin Y., and Kim D.H. Synlett (1998) 1189
76. Murakata M., Tsutsui H., and Hoshino O. Heterocycles 46 (1997) 517
77. Koenig T.M., and Mitchell D. Tetrahedron Lett. 35 (1994) 1339
78. Jenner G. Tetrahedron Lett. 42 (2001) 4807
79. Texier-Boullet F., and Foucaud A. Tetrahedron Lett. 23 (1982) 4927
80. Meschino J.A., and Bond C.H. J. Org. Chem. 28 (1963) 3129
81. Quirós M., Rebolledo F., Liz R., and Gotor V. Tetrahedron: Asymmetry 8 (1997) 3035
82. Kamila S., Zhu D., Biehl E.R., and Hua L. Org. Lett. 8 (2006) 4429