Catalytic asymmetric carbon-carbon bond formations: their evolution from biocatalysis to organocatalysis over the millennium

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 495-502

  Ikunaka, Masaya ^a  

^a Osaka City University Medical School   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 36448993162     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op050161t     Document Type: Review

References (62)

1. (a) Vasic-Racki, D. In Industrial Biotransformations, 2nd ed. completely revised and extended; Liese, A., Seelbach, K., Wandrey, C., Eds.; Wiley-VCH: Weinheim, 2006; pp 1-10.
2. (b) Liese, A.; Seelbach, K.; Buchholz, A.; Haberland, J. In Industrial Biotransformations, 2nd ed. completely revised and extended; Liese, A., Seelbach, K., Wandrey, C., Eds.; Wiley-VCH: Weinheim, 2006; pp 447-448.
3. (a) Pohl, A. Adv. Biochem. Eng. Biotechnol. 1997, 58, 15-43.
4. (b) Sprenger, G. A.; Pohl, M. J. Mol. Catal. B: Enzym. 1999, 6, 145-159.
5. (c) For benzoylformate decarboxylate (BFD) related to PDC, see: Iding, H.; Dünnwald, T.; Greiner, L.; Liese, A.; Müller, M.; Siegert, M.; Grötzinger, J.; Demir, A. S.; Pohl, M. Chem. - Eur. J. 2000, 6, 1483-1495.
6. Ikunaka, M.; Chikusa, Y.; Matsumoto, J.; Hirayama, Y. (Nagase & Co., Ltd.). WO 00/39071.
7. Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1998, 1891-1893.
8. (a) Mennen, S. M.; Blank, J. T.; Tran-Dubé, M. B.; Imbriglio, J. E.; Miller, S. J. Chem. Commun. 2005, 195-197.
9. (b) Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller, S. J. J. Am. Chem. Soc. 2005, 127, 1654-1655.
10. (c) Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
11. (d) Kerr, M. S.; Rovis, T. Synlett 2003, 1934-1936.
12. (e) de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 6284-6289.
13. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
14. (a) Shibasaki, M.; Iida, T.; Yamada, Y. M. A. J. Synth. Org. Chem. Jpn. (Yuki Gosei Kagaku Kyokaishi) 1998, 56, 344-356.
15. (b) Shibasaki, M.; Kanai, M. Chem. Pharm. Bull. 2001, 49, 511-356.
16. (c) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209.
17. (d) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491-1508.
18. (a) Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
19. (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198.
20. (c) Arai, T.; Sasaki, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
21. (d) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Oshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506-6507.
22. (e) Takita, R.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 466-14665.
23. (a) Shimizu, S.; Ohri, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 7547-7551.
24. (b) Xu, Y.; Ohri, K.; Ohshima, T.; Shibasaki, M. Tetrahedron 2002, 58, 2585-2588.
25. (c) Ohshima, T.; Xu, Y.; Takita, R.; Shimizu, S.; Zhong, D.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14546-14547.
26. (d) Ohshima, T.; Xu, Y.; Takita, R.; Shibasaki, M. Tetrahedron 2004, 60, 9569-9588.
27. (a) Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412-7413.
28. (b) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691-694.
29. Yabu, K.; Matsumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908-9909.
30. (a) Masumoto, S.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 8647-8651.
31. (b) Suzuki, M.; Kato, N.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 2527-2530.
32. Hayashi, M.; Inoue, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1994, 341-342.
33. (b) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385-4398.
34. Hayashi, M.; Kaneda, H.; Oguni, N. Tetrahedron: Asymmetry 1995, 6, 2511-2516.
35. Hayashi, M.; Yoshimoto, K.; Hirata, N.; Tanaka, K.; Oguni, N.; Harada, K.; Matsushita, A.; Kawachi, Y.; Sasaki, H. Isr. J. Chem. 2001, 41, 241-246.
36. Chen, L.; Dumas, D. P.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 241-246.
37. DeSantis, G.; Liu, J.; Clark, D. P.; Heine, A.; Wilson, I. A.; Wong, C.-H. Bioorg. Med. Chem. 2003, 11, 43-52.
38. (a) Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 8422-8423.
39. (b) Liu, J.; Wong, C.-H. Angew. Chem., Int. Ed. 2002, 41, 1404-1407.
40. Wong, C.-H.; Garcia-Junceda, E.; Chen, L.; Blanco, O.; Gijsen, H. J. M.; Steensma, D. H. J. Am. Chem. Soc. 1994, 116, 8422-8423.
41. Greenberg, W. A.; Varvak, A.; Hanson, S. R.; Wong, K.; Huang, H.; Chen, P.; Burk, M. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5788-5793.
42. For a compilation of chemoenzymatic approaches to statin side chains of the (3R)-syn-3,5-dihydroxy-6-substituted-hexanoate motif, see: Müller, M. Angew. Chem., Int. Ed. 2005, 44, 362-365.
43. (a) Kierkels, J. G. T.; Mink, D.; Panke, S.; Lommen, F. A. M.; Heemskerk, D. (DSM). WO 03/006656.
44. (b) Kooistra, J. M. H. H.; Zeegers, H. J. M.; Mink, D.; Mulders, J. M. C. A. (DSM). WO 02/06266.
45. (a) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229.
46. (b) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139-5151.
47. Kitamura, M.; Shirakawa, S.; Maruoka, K. Angew. Chem., Int. Ed. 2005, 44, 1549-1551.
48. Han, Z.; Yamaguchi, Y.; Kitamura, M.; Maruoka, K. Tetrahedron Lett. 2005, 46, 8555-8558.
49. Ooi, T.; Arimura, Y.; Hiraiwa, Y.; Yuan, L. M.; Kano, T.; Inoue, T.; Matsumoto, J.; Maruoka, K. Tetrahedron: Asymmetry 2006, 17, 603-606.
50. Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013-3028.
51. For the streamlined synthesis of 63 and 64, see: (a) Ooi, T.; Uematsu, Y.; Maruoka, K. J. Org. Chem. 2003, 68, 4576-4578.
52. (b) Ikunaka, M.; Maruoka, K.; Okuda, Y.; Ooi, T. Org. Process Res. Dev. 2003, 7, 644-648.
53. (c) Yamamoto, K.; Inoue, T.; Ikunaka, M. Abstract Papers of the 2005 Summer Symposium; the Japanese Society for Process Chemistry, Tokyo, July 28-29, 2005; the Japanese Society for Process Chemistry: Nagoya, 2005; pp 94-95.
54. Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
55. Kumar, S.; Ramachandran, U. Tetrahedron Lett. 2005, 46, 19-21.
56. Maeda, K.; Miller, R. A.; Szumigala, R. H., Jr.; Shafiee, A.; Karady, S.; Armstrong, J. D., III. Tetrahedron Lett. 2005, 46, 1545-1549.
57. Ooi, T.; Takeuchi, M.; Ohara, D.; Maruoka, K. Synlett 2001, 1185-1187.
58. Lee, Y.-J.; Lee, J.; Kim, M.-I.; Jeong, B.-S.; Lee, J.-H.; Kim, T.-S.; Lee, J.; Jew, S.; Park, H. Org. Lett. 2005, 7, 3207-3209.
59. For recent progress in the chemoenzymatic approaches to the chiral intermediates to build the side chains of synthetic statins, see: Thayer, A. N. Chem. Eng. News 2006, 84 (Aug 14), 26-27.
60. For Shibasaki's successful application of his concept of catalyst design to the synthesis of tamiflu, see: Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312-6313.
61. 2-symmetric chiral quaternary ammonium bromide 64 of a truncated structure, see ref 24.
62. 2-symmetric chiral quaternary ammonium bromides explored at Maruoka's laboratory, see: Ooi, T.; Takeuchi, M.; Kato, D.; Uematsu, Y.; Tayama, E.; Sakai, D.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 5073-5083.