Preparation of chiral organochalcogeno-α-methylbenzyl alcohols via biocatalysis. The role of Daucus carota root

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 473-476

  Comasseto, João V ^a   Omori, Álvaro T ^a   Porto, André L M ^a   Andrade, Leandro H ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

CAL B; Chiral alcohols; Daucus carota; Selenium; Sulfur

Indexed keywords

ACETOPHENONE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; CHALCOGEN; VEGETABLE PROTEIN;

ARTICLE; BIOCATALYST; CATALYSIS; CHIRALITY; ENANTIOMER; ENZYME KINETICS; GAS CHROMATOGRAPHY; PLANT ROOT; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM;

DAUCUS; DAUCUS CAROTA;

EID: 0346363696     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.011     Document Type: Article

References (45)

1. Mikolajczyk M., Drabowicz J., Kierlbasinski P. Chiral Sulfur Reagents: Applications in Asymmetric and Stereoselective Synthesis. 1997;CRC, Boca Raton.
2. (a) Wirth T. Tetrahedron. 55:1999;1.
3. (b) Wirth T. Top. Curr. Chem. 208:2000.
4. (c) Wirth T. Angew. Chem., Int. Ed. 39:2000;3740.
5. For a recent example, see: Tiecco M., Testaferri L., Santi C., Tomassini C., Marini F., Bagnoli L., Temperini A. Angew. Chem., Int. Ed. 42:2003;3131.
6. (a) Faber K. Biotransformations in Organic Chemistry. 4th ed. 2000;Springer, Berlin.
7. (b) Liese A., Seelbach K., Wandrey C. Industrial Biotransformations. 2000;Wiley-VCH, Weinheim.
8. (c) Roberts S.M. Biocatalysts for Fine Chemical Synthesis. 1999;John Wiley, New York.
9. Bruni R., Fantin G., Medici A., Pedrini P., Sacchetti G. Tetrahedron Lett. 43:2002;3377.
10. (b) Giri A., Dhingra V., Giri C.C., Singh A., Ward O.P., Narasu M.L. Biotechnol. Adv. 19:2001;175.
11. (a) Andrade L.H., Omori A.T., Porto A.L.M., Comasseto J.V. Tetrahedron: Asymmetry. 14:2003;711.
12. (b) Andrade L.H., Omori A.T., Porto A.L.M., Comasseto J.V. Chem. Listy. 2003;471.
13. Andrade L.H., Omori A.T., Porto A.L.M., Comasseto J.V. Chem. Listy. 2003;476.
14. For a recent review on the biocatalytic reduction of acetophenones, see: Nakamura K., Yamanaka R., Matsuda T., Harada T. Tetrahedron: Asymmetry. 14:2003;2659.
15. (a) Yadav J.S., Nanda S., Reddy P.T., Rao A.B. J. Org. Chem. 67:2002;3900. and references cited therein.
16. (b) Yadav J.S., Reddy P.T., Nanda S., Rao A.B. Tetrahedron: Asymmetry. 12:2001;3381
17. (c) Maczka W.A., Mironowicz A. Tetrahedron: Asymmetry. 13:2002;2299.
18. (a) Ferraboschi P., Grisenti P., Santaniello E. Synlett. 1990;545.
19. (b) Holland H.I., Carter I.M. Bioorg. Chem. 12:1983;1.
20. (c) Latham J.A., Branchaud B.P., Chen Y.C.J., Walsh C. J. Chem. Soc., Chem. Commun. 7:1986;528.
21. (d) Branchaud B.P., Walsh C.T. J. Am. Chem. Soc. 107:1985;2153.
22. (a) Silks L.A., Dunlap R.B., Odom J.D. J. Am. Chem. Soc. 112:1990;4979.
23. (b) Silks L.A., Peng J., Odom J.D., Dunlap R.B. J. Org. Chem. 56:1991;6733.
24. (c) Hedenstrom E., Nguyen B.-V., Silks L.A. Tetrahedron: Asymmetry. 13:2002;835.
25. For a recent example, see: Menezes P.H., Gonçalves S.M.C., Hallwass F., Silva R.O., Bieber L.W., Simas A.M. Org. Lett. 5:2003;1601.
26. For a review, see: Pu L., Yu H.-.B. Chem. Rev. 101:2001;757.
27. For a review, see: Luh T.-Y., Ni Z.-J. Synthesis. 1990;89. For a recent example, see: Alphonse F.-A., Suzenet F., Keromnes A., Lebret B., Guillaumet G. Org. Lett. 5:2003;803.
28. For a review, see: Luh T.-Y., Ni Z.-J. Synthesis. 1990;89. For a recent example, see: Alphonse F.-A., Suzenet F., Keromnes A., Lebret B., Guillaumet G. Org. Lett. 5:2003;803.
29. For an example, see: Okamura H., Miura M., Kosugi K., Takei H. Tetrahedron Lett. 21:1980;87.
30. 2-derivatives of tellurium with acetylenes mediated by Pd, see: Zeni G., Comasseto J.V. Tetrahedron Lett. 40:1999;4619. For a review, see: Zeni G., Braga A.L., Stefani H.A. Acc. Chem. Res. 36:2003;731. For similar reactions with vinylic selenides, see: Comasseto J.V., Ling L.W., Petragnani N., Stefani H.A. Synthesis. 1997;373.
31. 2-derivatives of tellurium with acetylenes mediated by Pd, see: Zeni G., Comasseto J.V. Tetrahedron Lett. 40:1999;4619. For a review, see: Zeni G., Braga A.L., Stefani H.A. Acc. Chem. Res. 36:2003;731. For similar reactions with vinylic selenides, see: Comasseto J.V., Ling L.W., Petragnani N., Stefani H.A. Synthesis. 1997;373.
32. 2-derivatives of tellurium with acetylenes mediated by Pd, see: Zeni G., Comasseto J.V. Tetrahedron Lett. 40:1999;4619. For a review, see: Zeni G., Braga A.L., Stefani H.A. Acc. Chem. Res. 36:2003;731. For similar reactions with vinylic selenides, see: Comasseto J.V., Ling L.W., Petragnani N., Stefani H.A. Synthesis. 1997;373.
33. Feugeas G. Bull. Soc. Chim. Fr. 11:1963;2573.
34. Wirth T., Fragale G. Chem. Eur. J. 3:1997;1894.
35. 10OSe: C, 50.72; H, 4.73.
36. 12OSe: C, 50.24; H, 5.62.
37. 3), ee=99%.
38. The (S)-3- and (S)-4-bromo-α-methylbenzyl alcohols were obtained by enzymatic kinetic resolution of the appropriate racemic mixture of meta- and para-bromo-α-methylbenzyl alcohols mediated by Novozym 435 (CAL-B) in tert-butyl methyl ether as the solvent and vinyl acetate as the acetyl donor. Further reaction of these chiral bromo precursors was carried out with t-BuLi followed by addition of the appropriate elemental chalcogen and methyl iodide or diphenyl diselenide to insert the organochalcogeno group. Andrade, L. H.; Omori, A. T.; Porto, A. L. M.; Comasseto, J. V., in press.
39. Prelog V. Pure Appl. Chem. 9:1964;119.
40. (a) For examples, see: Córdova A., Janda K.D. J. Org. Chem. 66:2001;1906 (b) Zhang Y., Yuan C., Li Z. Tetrahedron. 58:2002;2973 (c) Xu D., Li Z., Ma S. Tetrahedron Lett. 44:2003;6343.
41. (a) For examples, see: Córdova A., Janda K.D. J. Org. Chem. 66:2001;1906 (b) Zhang Y., Yuan C., Li Z. Tetrahedron. 58:2002;2973 (c) Xu D., Li Z., Ma S. Tetrahedron Lett. 44:2003;6343.
42. (a) For examples, see: Córdova A., Janda K.D. J. Org. Chem. 66:2001;1906 (b) Zhang Y., Yuan C., Li Z. Tetrahedron. 58:2002;2973 (c) Xu D., Li Z., Ma S. Tetrahedron Lett. 44:2003;6343.
43. 3), ee=98%. The chiral standards (S)-4a , (S)-4d and (S)-4g were prepared from (S)-1-phenylethanol using ortho-lithiation method with n-BuLi and TMEDA followed by addition of the appropriate elemental chalcogen and methyl iodide or diphenyl diselenide to insert the organochalcogeno group. Andrade, L. H.; Omori, A. T.; Porto, A. L. M.; Comasseto, J. V.; Cunha, R. L. O. R. Unpublished results.
44. Chen C.-S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294.
45. 77Se NMR spectra for substituted esters prepared with 4d.