Collect. Czech. Chem. Commun.
2005, 70, 1709-1726
https://doi.org/10.1135/cccc20051709
Toluene Dioxygenase-Mediated Oxidation of Bromo(methylsulfanyl)benzenes. Absolute Configuration of Metabolites and Evaluation of Chemo- and Regioselectivity Trends
Kevin J. Finn, Oksana Pavlyuk and Tomáš Hudlický*
Department of Chemistry, Brock University, St. Catharines, Ontario, Canada L2S 3A1
References
1. D. T., Koch J. R., Schuld C. L., Kallio R. E.: Biochemistry 1968, 7, 3795.
<https://doi.org/10.1021/bi00851a003>
2a. R. A.: Org. React. 2004, 63, 117.
2b. T., Gonzalez D., Gibson D. T.: Aldrichim. Acta 1999, 32, 35.
2c. D. R., Sheldrake G. N.: Nat. Prod. Rep. 1998, 15, 309.
<https://doi.org/10.1039/a815309y>
3a. Hudlický T., Reed J. W. in: Advances in Asymmetric Synthesis (A. Hassner, Ed.), p. 271. JAI Press, Greenwich, CT 1995.
3b. H. A. J.: Tetrahedron: Asymmetry 1992, 3, 795.
<https://doi.org/10.1016/S0957-4166(00)82174-6>
3c. D. A., Ribbons D. W., Thomas S. D.: Janssen Chim. Acta 1990, 8, 3.
3d. Sheldrake G. N. in: Chirality and Industry (A. N. Collins, G. N. Sheldrake and J. Crosby, Eds), p. 127. John Wiley and Sons, Ltd., Chichester, U.K. 1992.
3e. Brown S. M., Hudlický T. in: Organic Synthesis: Theory and Applications (T. Hudlicky, Ed.), Vol. 2, p. 113. JAI Press, Greewich, CT 1993.
3f. A. D.: SIMS News 1995, 45, 59.
3g. T.: Chem. Rev. 1996, 96, 3.
<https://doi.org/10.1021/cr950012g>
3h. T., Entwistle D. A., Pitzer K. K., Thorpe A. J.: Chem. Rev. 1996, 96, 1195.
<https://doi.org/10.1021/cr9403300>
3i. Hudlický T. in: Green Chemistry: Designing Chemistry for the Environment (P. T. Anastas and T. C. Williamson, Eds), Vol. 626, p. 180. ACS Symp. Ser., 1996.
3j. Hudlický T. in: Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes (P. T. Anastas and T. C. Williamson, Eds), Chap. 10, p. 166. Oxford University Press, Oxford, U.K. 1998.
4. G., Gibson D. T.: J. Biol. Chem. 1989, 264, 14940.
5. For indication of yields of more commonly used diols as well as a full description of medium-scale fermentation, see: M. A., Bui V. P., Hansen J., Hudlický T.: Org. Process Res. Dev. 2002, 6, 525.
<https://doi.org/10.1021/op020013s>
6. D. R., Sharma N. D., Byrne B. E., Haughey S. A., Kennedy M. A., Allen C. C. R.: Org. Biomol. Chem. 2004, 2, 2530.
<https://doi.org/10.1039/b409149c>
7a. D. R., Sharma N. D., Brannigan I. F., Haughey S. A., Malone J. F., Clarke D. A., Dalton H.: Chem. Commun. 1996, 2361.
<https://doi.org/10.1039/cc9960002361>
7b. D. R., Sharma N. D., Boyle R., McMurray B. T., Evans T. A., Malone J. F., Dalton H., Chima J., Sheldrake G. N.: J. Chem. Soc., Chem. Commun. 1993, 49.
<https://doi.org/10.1039/c39930000049>
7c. D. R., Sharma N. D., Boyle R., Evans T. A., Malone J. F., McCombe K. M., Dalton H., Chima J.: J. Chem. Soc., Perkin Trans. 1 1996, 1757.
<https://doi.org/10.1039/p19960001757>
7d. D. R., Sharma N. D., Hempenstall F., Kennedy M. A., Malone J. F., Allen C. C. R.: J. Org. Chem. 1999, 64, 4005.
<https://doi.org/10.1021/jo982517n>
7e. C. C. R., Boyd D. R., Dalton H., Sharma N. D., Haughey S. A., McMordie R. A. S., McMurray B. T., Sheldrake G. N., Sproule K.: J. Chem. Soc., Chem. Commun. 1995, 119.
<https://doi.org/10.1039/c39950000119>
8. K. J., Cankař P., Jones R. T. B., Hudlický T.: Tetrahedron: Asymmetry 2004, 15, 2833.
<https://doi.org/10.1016/j.tetasy.2004.06.050>
9. The optical purity was found to be greater than 90% based on comparison of optical rotation values for methyl phenyl sulfoxide found in the literature: H. L., Brown F. H., Larsen B. G.: Biorg. Med. Chem. Lett. 1994, 647.
<https://doi.org/10.1016/0968-0896(94)85013-5>
10. K., Brand J. M., Gibson D. T.: Biochem. Biophys. Res. Commun. 1995, 212, 9.
<https://doi.org/10.1006/bbrc.1995.1928>
11. T., Claeboe C. D., Brammer L. E., Koroniak L., Butora G., Ghiviriga I.: J. Org. Chem. 1999, 64, 4909.
<https://doi.org/10.1021/jo990382v>
12. D. R., Hand M. V., Sharma N. D., Chima J., Dalton H., Sheldrake G. N.: J. Chem. Soc., Chem. Commun. 1991, 1630.
<https://doi.org/10.1039/c39910001630>
13. Eliel E. L., Wilen S. H., Doyle M. P.: Basic Organic Stereochemistry, p. 443. John Wiley & Sons, Inc., New York 2001.
14. M., Cardellicchio C., Naso F., Tortorella P.: J. Org. Chem. 2000, 65, 2843.
<https://doi.org/10.1021/jo991912q>
15. Optical puritiy of 2-bromophenyl methyl sulfoxide: 93%, [α__MATH__ +32.5 (c 1.8, CHCl3) (lit.6 [α]D +35 (c 1.8, CHCl3)); optical purity of 3-bromophenyl methyl sulfoxide: 34%, [α__MATH__ +39.8 (c 1.2, acetone) (lit.14 [α]D +116.3 (c 1.2, acetone)).
16. N. A., Heck R. F.: J. Org. Chem. 1977, 42, 3491.
<https://doi.org/10.1021/jo00442a008>
17. The basic washing step was necessary since trace amounts of acid have been known to catalyze rapid and extremely exothermic dehydration and aromatization of cis- cyclohexadienediols.
18. D. R., Sharma N. D., Byrne B., Hand M. V., Malone J. F., Sheldrake G. N., Blacker J., Dalton H.: J. Chem. Soc., Perkin Trans. 1 1998, 1935.
<https://doi.org/10.1039/a800809d>
19. V. P., Nguyen M., Hansen J., Baker J., Hudlicky T.: Can. J. Chem. 2002, 80, 708.
<https://doi.org/10.1139/v02-098>
20. T., Oppong K., Duan C., Stanton C., Laufensweiler M. J., Natchus M. G.: Biorg. Med. Chem. Lett. 2001, 11, 627.
<https://doi.org/10.1016/S0960-894X(01)00013-0>

