Practical asymmetric hydrogenation of 3-quinuclidinone catalyzed by the xylskewphos/PICA-ruthenium(II) complex

Organic Process Research and Development

Volumn 13, Issue 3, 2009, Pages 625-628

  Tsutsumi, Kunihiko ^b   Katayama, Takeaki ^b   Utsumi, Noriyuki ^b   Murata, Kunihiko ^b   Arai, Noriyoshi ^a   Kurono, Nobuhito ^a   Ohkuma, Takeshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KANTO CHEMICAL CO INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66249085533     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op9000302     Document Type: Article

References (60)

1. Naito, R.; Yonetoku, Y.; Okamoto, Y.; Toyoshima, A.; Ikeda, K.; Takeuchi, M. J. Med. Chem. 2005, 48, 6597-6606.
2. Alabaster, V. A. Life Sci. 1997, 60, 1053-1060.
3. Leusch, A.; Tröger, W.; Greischel, A.; Roth, W. Xenobiotica 2000, 30, 797-813.
4. (a) Rehavi, M.; Maayani, S.; Sokolovsky, M. Life Sci. 1977, 21, 1293- 1302.
5. Muchmore, D. C. U.S. Patent 5,215,918 A 19930601, 1993; Chem. Abstr. 1993, 119, 135038.
6. Sato, E.; Enomoto, K. Chem. Abstr. 1998, 129, 15355; PCT Int. WO 9820152 A1 19980514, 1998.
7. Nomoto, F.; Otsuka, K. Chem. Abstr. 1998, 129, 188419; Jpn. Kokai Tokkyo Koho 10210997 A 19980811 Heisei, 1998.
8. Primozic, I.; Hrenar, T.; Tomic, S.; Meic, Z. Eur. J. Org. Chem. 2003, 295-301.
9. (a) Nomoto, F.; Hirayama, Y.; Ikunaka, M.; Inoue, T.; Otsuka, K. Tetrahedron: Asymmetry 2003, 14, 1871-1877.
10. Chikusa, Y.; Hirayama, Y.; Ikunaka, M.; Inoue, T.; Kamiyama, S.; Moriwaki, M.; Nishimoto, Y.; Nomoto, F.; Ogawa, K.; Ohno, T.; Otsuka, K.; Satoka, A. K.; Shirasaka, N.; Uzura, A.; Uzura, K. Org. Process Res. Dev. 2003, 7, 289-296.
11. Ikunaka, M. Catal. Today 2004, 96, 93-102.
12. (a) Matsuyama, A.; Hamatani, T. Eur. Patent 863212 A2 19980909, 1998; Chem. Abstr. 1998, 129, 229744.
13. Nomoto, F.; Kuramura, A.; Otsuka, K. Chem. Abstr. 1999, 131, 101312; Jpn. Kokai Tokkyo Koho 11196890 A 19990727 Heisei, 1999.
14. Goto, M.; Ueda, M. Chem. Abstr. 2000, 133, 221696; Jpn. Kokai Tokkyo Koho 2000245495 A 20000912, 2000.
15. Ito, S. Chem. Abstr. 2002, 136, 400696; Jpn. Kokai Tokkyo Koho 2002153293 A 20020528, 2002.
16. Yamamoto, H.; Ueda, M.; Ritsuzui, P.; Hamatani, T. Eur. Patent 1318200 A2 20030611, 2003; Chem. Abstr. 2003, 139, 35200.
17. Ito, S. Chem. Abstr. 2003, 139, 377253; Jpn. Kokai Tokkyo Koho 2003334069 A 20031125, 2003.
18. Garci'a-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313-354.
19. Uzura, A.; Nomoto, F.; Sakoda, A.; Nishimoto, Y.; Kataoka, M.; Shimizu, S. Appl. Microbiol. Biotechnol. 2009. Published online 21 February.
20. Miscellaneous methods for the synthesis of (R)-2: (a) Sternbach, L. H.; Kaiser, S. J. Am. Chem. Soc. 1952, 74, 2215-2218.
21. Ringdahl, B.; Resul, B.; Dahlbom, R. Acta Pharm. Suec. 1979, 16, 281-283.
22. Knight, D. W.; Lewis, N.; Share, A. C.; Haigh, D. J. Chem. Soc. Perkin Trans. 1 1998, 3673-3683.
23. Bjørsvik, H.-R.; Liguori, L.; Costantino, F.; Minisci, F. Org. Process Res. Dev. 2002, 6, 197-200.
24. Simeon- Rudolf, V.; Tomic, S.; Bosak, A.; Primozic, I.; Orsulic, M. Chem. Biol. Interact. 2005, 157-158, 420-421.
25. Reviews on asymmetric hydrogenation of ketones: (a) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin-Heidelberg, 1999; Vol. 1, pp 199-246.
26. Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110.
27. Ohkuma, T.; Noyori, R. In Transition Metals for Organic Synthesis; 2nd ed.;Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 29-113.
28. Ohkuma, T.; Noyori, R. In The Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, 2007; Vol. 3, pp 1105-1163.
29. (a) Takenaka, M. Chem. Abstr. 2005, 143, 422509; Jpn. Kokai Tokkyo Koho 2005306804 A 20051104, 2005. See also:
30. Aoki, T. Chem. Abstr. 2003, 139, 277052; Jpn. Kokai Tokkyo Koho 2003277380 A 20031002, 2003.
31. For asymmetric hydrogenation of 1 with chiral Rh(I) catalysts, see: (a) Brieden, W. Eur. Patent 785198 A1 19970723, 1997; Chem. Abstr. 1997, 127, 176346.
32. Ito, T.; Aoki, T. Chem. Abstr. 2004, 141, 260264; PCT Int. WO 2004078686 A1 20040916, 2004.
33. Blaser, H.-U.; Pugin, B.; Spindler, F. In Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 2002; Vol. 3, pp 1131-1149.
34. For BINAP/chiral ethylenediamine-Ru(II) systems, see: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676.
35. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417-10418.
36. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872-4873.
37. Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468.
38. Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703-1707.
39. Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529-13530.
40. Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
41. Ohkuma, T.; Koizumi, M.; Yoshida, M.; Noyori, R. Org. Lett. 2000, 2, 1749-1751.
42. Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510-6511.
43. Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369-375.
44. Ohkuma, T.; Koizumi, M.; Muñiz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508-6509.
45. Ohkuma, T.; Li, J.; Noyori, R. Synlett 2004, 1383-1386.
46. For BINAP/chiral 1,4-diamine-Ru(II) systems, see: Ohkuma, T.; Hattori, T.; Ooka, H.; Inoue, T.; Noyori, R. Org. Lett. 2004, 6, 2681- 2683.
47. For BINAP/chiral N,N-dimethylethylenediamine-Ru(II) systems, see: (a) Arai, N.; Ooka, H.; Azuma, K.; Yabuuchi, T.; Kurono, N.; Inoue, T.; Ohkuma, T. Org. Lett. 2007, 9, 939-941.
48. Arai, N.; Azuma, K.; Nii, N.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 7457- 7460.
49. Ooka, H.; Arai, N.; Azuma, K.; Kurono, N.; Ohkuma, T. J. Org. Chem. 2008, 73, 9084-9093.
50. Reviews: (a) Ohkuma, T. J. Synth. Org. Chem. Jpn. 2007, 65, 1070- 1080.
51. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73.
52. (a) Ohkuma, T.; Sandoval, C. A.; Srinivasan, R.; Lin, Q.; Wei, Y.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2005, 127, 8288-8289.
53. Arai, N.; Suzuki, K.; Sugizaki, S.; Sorimachi, H.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 1770-1773.
54. Baratta, W.; Herdtweck, E.; Siega, K.; Toniutti, M.; Rigo, P. Organometallics 2005, 24, 1660-1669.
55. (a) McKinstry, L.; Livinghouse, T. Tetrahedron 1995, 51, 7655-7666.
56. Hu, W.; Pai, C. C.; Chen, C. C.; Xue, G.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 3241-3246.
57. Tsutsumi, K.; Murata, K.; Ota, T.; Ikariya, T. Chem. Abstr. 2003, 139, 133671; Jpn. Kokai Tokkyo Koho 2003206295 A 20030722, 2003.
58. Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675-690.
59. Complex 4 was obtained as a mixture of five diastereomers (see ref 16 for details), while the catalytic activity and enantioselectivity were independent of the initial diastereomeric ratio.
60. The integration number of aromatic protons was less than the actual one. This may have been caused by their slow relaxation.