Access to optically pure 4- and 5-substituted lactones: A case of chemical-biocatalytical cooperation

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6222-6228

  Wang, Shaozhao ^a   Kayser, Margaret M ^a   Jurkauskas, Valdas ^b  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCATALYSTS; ENZYMES; ESCHERICHIA COLI; OXIDATION;

CATALYZED OXIDATION;

KETONES;

CYCLOPENTANONE DERIVATIVE; CYCLOPENTANONE MONOOXYGENASE; KETONE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ESCHERICHIA COLI; NONHUMAN; OPTICS; OXIDATION; STRUCTURE ANALYSIS; SYNTHESIS;

CATALYSIS; INDICATORS AND REAGENTS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION;

EID: 0041529886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026605q     Document Type: Article

References (51)

1. For reviews on chemical Baeyer-Villiger oxidations, see: (a) Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1199-1209. (b) Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737-750.
2. For reviews on chemical Baeyer-Villiger oxidations, see: (a) Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1199-1209. (b) Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737-750.
3. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
4. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
5. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
6. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
7. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
8. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
9. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
10. For recent examples on chemical Baeyer-Villiger oxidations, see: (a) Neimann, K.; Neumann, R. Org. Lett. 2000, 2, 2861-2863. (b) Lambert, A.; Elings, J. A.; Macquarrie, D. J.; Carr, G.; Clark, J. H. Synlett 2000, 1052-1054. (c) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433. (d) Corma, A.; Nemeth, L. T.; Renz, M.; Valencia, S. Nature 2001, 412, 423-425. (e) Berkessel, A.; Andreae, M. R. M. Tetrahedron Lett. 2001, 42, 2293-2295. (f) Bolm, C.; Palazzi, C.; Francio, G.; Leitner, W. Chem. Commun. 2002, 1588-1589. (g) Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368. (h) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
11. For reviews on enzyme-catalyzed Baeyer-Villiger oxidations, see: (a) Stewart, J. D. Curr. Org. Chem. 1998, 2, 195-216. (b) Leonida, M. D. Curr. Med. Chem. 2001, 8, 345-369.
12. For reviews on enzyme-catalyzed Baeyer-Villiger oxidations, see: (a) Stewart, J. D. Curr. Org. Chem. 1998, 2, 195-216. (b) Leonida, M. D. Curr. Med. Chem. 2001, 8, 345-369.
13. For recent examples on enzyme-catalyzed Baeyer-Villiger oxidations, see: (a) Sheng, D.; Ballou, D. P.; Massey, V. Biochemistry 2001, 40, 11156-11167. (b) Colonna, S.; Del Sordo, S.; Gaggero, N.; Carrea, G.; Pasta, P. Heteroatom Chem. 2002, 13, 467-473.
14. For recent examples on enzyme-catalyzed Baeyer-Villiger oxidations, see: (a) Sheng, D.; Ballou, D. P.; Massey, V. Biochemistry 2001, 40, 11156-11167. (b) Colonna, S.; Del Sordo, S.; Gaggero, N.; Carrea, G.; Pasta, P. Heteroatom Chem. 2002, 13, 467-473.
15. Stewart, J. D.; Reed, K. W.; Martinez, C. A.; Zhu, J.; Chen, G.; Kayser, M. M. J. Am. Chem. Soc. 1998, 120, 3541-3548.
16. Kayser, M. M.; Chen, G.; Stewart, J. D. J. Org. Chem. 1998, 63, 7103-7106.
17. (a) Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 30, 3663-3664.
18. (b) Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382.
19. Leading references on kinetic resolution: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330. (b) Kagan, H. B. Tetrahedron 2001, 57, 2449-2468. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26. (d) Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 545-553. For recent treatment of biocatalytic aspects of kinetic resolution see: Faber, K.; Kroutil, W. Tetrahedron: Asymmetry 2002, 13, 377-382.
20. Leading references on kinetic resolution: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330. (b) Kagan, H. B. Tetrahedron 2001, 57, 2449-2468. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26. (d) Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 545-553. For recent treatment of biocatalytic aspects of kinetic resolution see: Faber, K.; Kroutil, W. Tetrahedron: Asymmetry 2002, 13, 377-382.
21. Leading references on kinetic resolution: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330. (b) Kagan, H. B. Tetrahedron 2001, 57, 2449-2468. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26. (d) Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 545-553. For recent treatment of biocatalytic aspects of kinetic resolution see: Faber, K.; Kroutil, W. Tetrahedron: Asymmetry 2002, 13, 377-382.
22. Leading references on kinetic resolution: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330. (b) Kagan, H. B. Tetrahedron 2001, 57, 2449-2468. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26. (d) Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 545-553. For recent treatment of biocatalytic aspects of kinetic resolution see: Faber, K.; Kroutil, W. Tetrahedron: Asymmetry 2002, 13, 377-382.
23. Leading references on kinetic resolution: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330. (b) Kagan, H. B. Tetrahedron 2001, 57, 2449-2468. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26. (d) Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 545-553. For recent treatment of biocatalytic aspects of kinetic resolution see: Faber, K.; Kroutil, W. Tetrahedron: Asymmetry 2002, 13, 377-382.
24. Reviews on conjugate addition: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (c) Hayashi, T. Synlett 2001, 879-887.
25. Reviews on conjugate addition: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (c) Hayashi, T. Synlett 2001, 879-887.
26. Reviews on conjugate addition: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (c) Hayashi, T. Synlett 2001, 879-887.
27. For recent examples of enantioselective conjugate addition to cyclic enones, see: (a) Arnold, L. A.; Imbos, R.; Mandoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865-2878. (b) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (e) Reetz, M. T.; Gosberg, A.; Moulin, D. Tetrahedron Lett. 2002, 43, 1189-1191.
28. For recent examples of enantioselective conjugate addition to cyclic enones, see: (a) Arnold, L. A.; Imbos, R.; Mandoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865-2878. (b) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (e) Reetz, M. T.; Gosberg, A.; Moulin, D. Tetrahedron Lett. 2002, 43, 1189-1191.
29. For recent examples of enantioselective conjugate addition to cyclic enones, see: (a) Arnold, L. A.; Imbos, R.; Mandoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865-2878. (b) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (e) Reetz, M. T.; Gosberg, A.; Moulin, D. Tetrahedron Lett. 2002, 43, 1189-1191.
30. For recent examples of enantioselective conjugate addition to cyclic enones, see: (a) Arnold, L. A.; Imbos, R.; Mandoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865-2878. (b) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (e) Reetz, M. T.; Gosberg, A.; Moulin, D. Tetrahedron Lett. 2002, 43, 1189-1191.
31. For recent examples of enantioselective conjugate addition to cyclic enones, see: (a) Arnold, L. A.; Imbos, R.; Mandoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865-2878. (b) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (e) Reetz, M. T.; Gosberg, A.; Moulin, D. Tetrahedron Lett. 2002, 43, 1189-1191.
32. Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797-6798. For application of asymmetric conjugate reduction to disubstituted cyclopentenones, see: Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892-2893.
33. Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797-6798. For application of asymmetric conjugate reduction to disubstituted cyclopentenones, see: Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892-2893.
34. Compounds (R)-1b and (R)-4b were a gift from Drs. Escher and Pfaltz, who synthesized them via 1,4-additions of organozinc reagents to cyclic enones. See ref 10b.
35. Mihovilovic, M. D.; Chen, G.; Wang, S.; Kyte, B.; Rochon, F.; Kayser, M. M.; Stewart, J. D. J. Org. Chem. 2001, 66, 733-738.
36. Iwaki, H.; Hasegawa, Y.; Wang, S. Z.; Kayser, M. M.; Lau, P. C. K. Appl. Environ. Microbiol. 2002, 68, 5671-5684.
37. The hydroxy acids were not detectable on GC since at high temperature they undergo condensation to yield the corresponding lactones.
38. Wang, S. Z.; Chen, G.; Kayser, M. M.; Iwaki, H.; Lau, P. C. K.; Hasegawa, Y. Can. J. Chem. 2002, 80, 613-621.
39. Mihovilovic M. D.; Müller, B.; Kayser, M. M.; Stanetty, P. Synlett 2002, 700-703.
40. (a) Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
41. (b) Alaimo, P. J.; Peters, D. W.; Arnold, J.; Bergman, R. G. J. Chem. Educ. 2001, 78, 64.
42. Strok, G.; Danheiser, R. L. Org. Chem. 1973, 38, 1775-1776.
43. Jones, P.; Reddy, C. K.; Knochel, P. Tetrahedron 1998, 54, 1471-1490.
44. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821-1830.
45. Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
46. Gadwood, R. C.; Mallick, I. M.; DeWinter, A. J. J. Org. Chem. 1987, 52, 774-782.
47. (a) Oikawa, M.; Oikawa, H.; Ichihara, A. Tetrahedron 1995, 51, 6237-6254.
48. (b) Ozegowski, R.; Kunath, A.; Schick, H. Liebigs Ann. Chem. Engl. 1994, 10, 1019-1023.
49. Ashworth, P.; Belagali, S. L.; Casson, S.; Marczak, A.; Kocienski, P. Tetrahedron 1991, 47, 9939-9946.
50. Hiratake, J.; Yamamoto, K.; Yamamoto, Y.; Oda, J. Tetrahedron Lett. 1989, 30, 1555-1556.
51. Paquette, L. A.; Dahnke, K.; Doyon, J.; He, W.; Wyant, K.; Friedrich, D. J. Org. Chem. 1991, 56, 6199-6205.