A highly enantioselective catalytic desymmetrization of cyclic anhydrides with modified cinchona alkaloids [3]

Journal of the American Chemical Society

Volumn 122, Issue 39, 2000, Pages 9542-9543

  Chen, Yonggang ^a   Tian, Shi Kai ^a   Deng, Li ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; CARBONYL DERIVATIVE; CINCHONA ALKALOID;

CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; HYDROXYLATION; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0034605437     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001765+     Document Type: Letter

References (43)

1. Toyota, M.; Yokota, M.; Ihara, M. Org. Lett. 1999, 1, 1627.
2. Couche, E.; Deschatrettes, R.; Poumellec, K.; Bortolussi, M.; Mandvile, G.; Bloch, R. Synlett 1999, 87.
3. Paterson, I.; Cowden, C. J.; Woodrow, M. D. Tetrahedron Lett. 1998, 39, 6037.
4. (a) Borzilleri, R. B.; Weiareb, S. M. J. Am. Chem. Soc. 1994, 116, 9789.
5. (b) Borzilleri, R. B.; Weinreb, S. M.; Parvez, M. J. Am. Chem. Soc. 1995, 117, 10905.
6. Marie, F. B. C.; Mackiewicz, P.; Roul, J. M.; Buendia, J. Tetrahedron Lett. 1992, 33, 4889.
7. (a) Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 4120.
8. (b) Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 2122.
9. Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1990, 31, 2517.
10. Suzuki, T.; Tomino, A.; Matsuda, Y.; Unno, K.; Kametani, T. Heterocycle 1980, 14, 1735.
11. (a) Heathcock, C. H.; Hadley, C. R.; Rosen, T.; Theisen, P. D.; Hecker, S. J. J. Med. Chem. 1987, 30, 1858.
12. (b) Hecker, S. J.; Heathcock, C. H. J. Am. Chem. Soc. 1986, 108, 4586.
13. (c) Rosen, T.; Heathcock, C. H. J. Am. Chem. Soc. 1985, 107, 3731.
14. For a recent review see: Willis, M. C. J. Chem. Soc., Perkins Tran. 1 1999, 1765.
15. For representative examples of chiral auxiliary-based methods see: (a) Albers, T.; Biagini, S. C. G.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A.; North, M.; Uriarte, E.; Zagotto, G. Synthesis 1996, 393. (b) Konoike, T.; Araki, Y. J. Org. Chem. 1994, 59, 7849. (c) Shimizu, M.; Matsukawa, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1993, 66, 2128. (d) Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1993, 58, 142.
16. For representative examples of chiral auxiliary-based methods see: (a) Albers, T.; Biagini, S. C. G.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A.; North, M.; Uriarte, E.; Zagotto, G. Synthesis 1996, 393. (b) Konoike, T.; Araki, Y. J. Org. Chem. 1994, 59, 7849. (c) Shimizu, M.; Matsukawa, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1993, 66, 2128. (d) Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1993, 58, 142.
17. For representative examples of chiral auxiliary-based methods see: (a) Albers, T.; Biagini, S. C. G.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A.; North, M.; Uriarte, E.; Zagotto, G. Synthesis 1996, 393. (b) Konoike, T.; Araki, Y. J. Org. Chem. 1994, 59, 7849. (c) Shimizu, M.; Matsukawa, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1993, 66, 2128. (d) Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1993, 58, 142.
18. For representative examples of chiral auxiliary-based methods see: (a) Albers, T.; Biagini, S. C. G.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A.; North, M.; Uriarte, E.; Zagotto, G. Synthesis 1996, 393. (b) Konoike, T.; Araki, Y. J. Org. Chem. 1994, 59, 7849. (c) Shimizu, M.; Matsukawa, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1993, 66, 2128. (d) Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1993, 58, 142.
19. For the most successful examples of chiral mediator-based methods see: (a) Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395. (b) Jaeschke, G.; Seebach, D. J. Org. Chem. 1998, 63, 1190. (c) Bolm, C.; Gerlach, A.; Dinter, C. L. Synlett 1999, 195.
20. For the most successful examples of chiral mediator-based methods see: (a) Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395. (b) Jaeschke, G.; Seebach, D. J. Org. Chem. 1998, 63, 1190. (c) Bolm, C.; Gerlach, A.; Dinter, C. L. Synlett 1999, 195.
21. For the most successful examples of chiral mediator-based methods see: (a) Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395. (b) Jaeschke, G.; Seebach, D. J. Org. Chem. 1998, 63, 1190. (c) Bolm, C.; Gerlach, A.; Dinter, C. L. Synlett 1999, 195.
22. (a) Hiratake, J.; Yamamoto, Y.; Oada, J. J. Chem. Soc., Chem. Commun. 1985, 1717.
23. (b) Hiratake, J.; Inagaki, M.; Yamamoto, Y.; Oada, J. J. Chem. Soc., Perkin. Trans, 1 1987, 1053.
24. (a) Aitken, R. A.; Gopal, J.; Hirst, J. A. J. Chem. Soc. Chem. Commun. 1988, 632.
25. (b) Aitken, R. A.; Gopal, J. Tetrahedron: Asymmetry 1990, 1, 517.
26. For enzyme-catalyzed alcoholysis of cyclic anhydrides see: (a) Ozegowski, R.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1191. (b) Yamamoto, K.; Nishioka, T.; Oada, J. Tetrahedron Lett. 1988, 29, 1717. (c) Yamamoto, Y.; Yamamoto, K.; Nishioka, T.; Oada, J. Agric. Biol. Chem. 1988, 52, 3087.
27. For enzyme-catalyzed alcoholysis of cyclic anhydrides see: (a) Ozegowski, R.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1191. (b) Yamamoto, K.; Nishioka, T.; Oada, J. Tetrahedron Lett. 1988, 29, 1717. (c) Yamamoto, Y.; Yamamoto, K.; Nishioka, T.; Oada, J. Agric. Biol. Chem. 1988, 52, 3087.
28. For enzyme-catalyzed alcoholysis of cyclic anhydrides see: (a) Ozegowski, R.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1191. (b) Yamamoto, K.; Nishioka, T.; Oada, J. Tetrahedron Lett. 1988, 29, 1717. (c) Yamamoto, Y.; Yamamoto, K.; Nishioka, T.; Oada, J. Agric. Biol. Chem. 1988, 52, 3087.
29. For a Lewis base-catalyzed highly enantioselective acylation of meso diols see: Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794.
30. For leading references see: (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M; Xu, D.; Zhang, X.-L. J. Org. Chem. 1991, 56, 4585. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785. (d) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (e) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (f) Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer: Heidelberg, 1999; Chapter 20.
31. For leading references see: (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M; Xu, D.; Zhang, X.-L. J. Org. Chem. 1991, 56, 4585. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785. (d) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (e) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (f) Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer: Heidelberg, 1999; Chapter 20.
32. For leading references see: (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M; Xu, D.; Zhang, X.-L. J. Org. Chem. 1991, 56, 4585. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785. (d) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (e) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (f) Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer: Heidelberg, 1999; Chapter 20.
33. For leading references see: (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M; Xu, D.; Zhang, X.-L. J. Org. Chem. 1991, 56, 4585. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785. (d) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (e) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (f) Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer: Heidelberg, 1999; Chapter 20.
34. For leading references see: (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M; Xu, D.; Zhang, X.-L. J. Org. Chem. 1991, 56, 4585. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785. (d) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (e) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (f) Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer: Heidelberg, 1999; Chapter 20.
35. For leading references see: (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M; Xu, D.; Zhang, X.-L. J. Org. Chem. 1991, 56, 4585. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785. (d) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (e) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (f) Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer: Heidelberg, 1999; Chapter 20.
36. (a) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069.
37. (b) Kolb, H. C.; Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 1278.
38. (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579.
39. (b) Corey, E. J.; Noe, M. C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861.
40. (c) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 319.
41. (d) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038.
42. For excellent reviews of enzyme-catalyzed hydrolysis of meso-diesters see: (a) Zhu, L.-M.; Tedford, M. C. Tetrahedron, 1990, 46, 6587-6611. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd: Oxford, 1994; Vol. 12, pp 41-87.
43. For excellent reviews of enzyme-catalyzed hydrolysis of meso-diesters see: (a) Zhu, L.-M.; Tedford, M. C. Tetrahedron, 1990, 46, 6587-6611. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd: Oxford, 1994; Vol. 12, pp 41-87.