Biocatalysis in Organic Synthesis. 9. Highly Enantioselective Kinetic Resolution of Secondary Alcohols Catalyzed by Acylase

Synlett

Volumn 1997, Issue 4, 1997, Pages 367-370

  Faraldos, Juan ^a   Arroyo, Elisa ^a   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001495722     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-796     Document Type: Article

References (38)

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2. (b) Part 8: Noheda, P.; García, G.; Pozuelo, M. C.; Herradón, B. Tetrahedron: Asymmetry 1996, 7, 2801-2804. (c) Taken from the master's thesis of J. F. and E. A.
3. (b) Part 8: Noheda, P.; García, G.; Pozuelo, M. C.; Herradón, B. Tetrahedron: Asymmetry 1996, 7, 2801-2804. (c) Taken from the master's thesis of J. F. and E. A.
4. Enzyme Catalysis in Organic Synthesis. A Comprehensive Handbook; Drauz. K.; Waldmann, H., Eds.; VCH: Weinheim; 1995.
5. Seebach, D.; Hungerbühler, E. In Modern Synthetic Methods; Scheffold, R., Ed.; Salle and Saueländer: Berlin; 1980; Vol 2, pp 91-171.
6. The issue of the modulation of the selectivity upon changes in the experimental conditions (experimental modulation of the selectivity) in biocatalytic transformations have been discussed elsewhere, see: Herradón, B.; Valverde, S. Tetrahedron: Asymmetry 1994, 5, 1479-1500.
7. Chenault, H. K.; Dahmer, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354-6364.
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9. (a) Sih, C. J.; Wu, S. H. Topics Stereochem. 1989, 19, 63-125.
10. (b) The figures into brackets indicate the actual values of E calculated according to ref 7a. Values of E > 100 should be judged with care because they are sensitive to small errors in measurements of enantiomeric excesses.
11. These stationary phases have been prepared by Mrs. Ma Isabel Jiménez (Instituto de Química Orgánica General. C. S. I. C.). to whom we thank for her assistance on the glc analysis.
12. 3, c = 0.5).
13. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
14. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
15. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
16. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
17. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
18. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
19. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
20. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
21. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
22. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
23. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
24. For recent papers dealing with the syntheses of some of these chiral building blocks, see: Ikeda, N.; Arai, I.; Yamamoto. H. J. Am. Chem. Soc. 1986, 108, 483-486. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97-100. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-562. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676. Suginaka, K.; Hayashi, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1996, 7, 1153-1158. Newman, L. M., Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195. Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217-1218. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
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30. For some recent examples, see: Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442-444. Fronza, G.; Fuganti, C.; Grasselli, P.; Mele, A. J. Org. Chem. 1991, 56, 6019-6023. Akita, H.; Chen, C. Y.; Uchida, K. Tetrahedron: Asymmetry 1995, 6, 2131-2134. Perricone, S. C.; Chidester, C. G.; Hester, J. B. Tetrahedron: Asymmetry 1996, 7, 677-690. Ramacciotti, A.; Fiaschi, R.; Napolitano, E. Tetrahedron: Asymmetry 1996, 7, 1101-1104.
31. For some recent examples, see: Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442-444. Fronza, G.; Fuganti, C.; Grasselli, P.; Mele, A. J. Org. Chem. 1991, 56, 6019-6023. Akita, H.; Chen, C. Y.; Uchida, K. Tetrahedron: Asymmetry 1995, 6, 2131-2134. Perricone, S. C.; Chidester, C. G.; Hester, J. B. Tetrahedron: Asymmetry 1996, 7, 677-690. Ramacciotti, A.; Fiaschi, R.; Napolitano, E. Tetrahedron: Asymmetry 1996, 7, 1101-1104.
32. For some recent examples, see: Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442-444. Fronza, G.; Fuganti, C.; Grasselli, P.; Mele, A. J. Org. Chem. 1991, 56, 6019-6023. Akita, H.; Chen, C. Y.; Uchida, K. Tetrahedron: Asymmetry 1995, 6, 2131-2134. Perricone, S. C.; Chidester, C. G.; Hester, J. B. Tetrahedron: Asymmetry 1996, 7, 677-690. Ramacciotti, A.; Fiaschi, R.; Napolitano, E. Tetrahedron: Asymmetry 1996, 7, 1101-1104.
33. For some recent examples, see: Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442-444. Fronza, G.; Fuganti, C.; Grasselli, P.; Mele, A. J. Org. Chem. 1991, 56, 6019-6023. Akita, H.; Chen, C. Y.; Uchida, K. Tetrahedron: Asymmetry 1995, 6, 2131-2134. Perricone, S. C.; Chidester, C. G.; Hester, J. B. Tetrahedron: Asymmetry 1996, 7, 677-690. Ramacciotti, A.; Fiaschi, R.; Napolitano, E. Tetrahedron: Asymmetry 1996, 7, 1101-1104.
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38. 5 we hypothesize that the enzyme possesses a second active centre with esterase-like activity, which is responsible of the acylation reaction (i. e., similar to a serine protease). Work is in progress in order to understand the mechanism of this new reaction.