Asymmetric hydrogenation of amino ketones using chiral RuCl2(diphophine)(1,2-diamine) complexes [12]

Journal of the American Chemical Society

Volumn 122, Issue 27, 2000, Pages 6510-6511

  Ohkuma, Takeshi ^a   Ishii, Dai ^a   Takeno, Hiroshi ^a   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOKETONE; PHOSPHINE; RHODIUM COMPLEX; RUTHENIUM COMPLEX;

CATALYST; CHELATION; CRYSTALLIZATION; CYCLIZATION; HYDROGENATION; HYDROLYSIS; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TEMPERATURE;

EID: 0034641294     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001098k     Document Type: Letter

References (34)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; Chapter 2.
2. (a) Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 425-428.
3. (b) Torös, S.; Kollár, L.; Heil, B.; Markó, L. J. Organomet. Chem. 1982, 232, C17-C18.
4. (c) Yoshikawa, K.; Yamamoto, N.; Murata, M.; Awano, K.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1992, 3, 13-16.
5. (d) Devocelle, M.; Agbossou, F.; Mortreux, A. Synlett 1991, 1306-1308.
6. (e) Pasquier, C.; Naili, S.; Pelinski, L.; Brocard, J.; Mortreux, A.; Agbossou, F. Tetrahedron: Asymmetry 1998, 9, 193-196.
7. (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629-631.
8. (b) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064-3076.
9. Takeda, H.; Tachinami, T.; Aburatani, M.; Takahashi, H.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1989, 30, 363-366.
10. For Rh-catalyzed hydrogenation at atmospheric pressure (S/C = 200), see: Devocelle, M.; Mortreux, A.; Agbossou, F.; Dormoy, J.-R. Tetrahedron Lett. 1999, 40, 4551-4554.
11. (a) Sakuraba, S.; Achiwa, K. Synlett 1991, 689-690.
12. (b) Sakuraba, S.; Nakajima, N.; Achiwa, K. Synlett 1992, 829-830.
13. Fur example: (a) 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. (b) 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. (c) Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
14. Fur example: (a) 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. (b) 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. (c) Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
15. Fur example: (a) 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. (b) 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. (c) Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
16. Noyori, R.; Ohkuma, T. Pure Appl. Chem. 1999, 71, 1493-1501 and references therein.
17. 3b DAIPEN = 1,1-di(4-anisyl)-2-isopropyl-1,2-ethylenediamine.
18. In going from 1-phenylethanol to the amino alcohols 5, the R,S nomenclature is reversed by the change of atom priority.
19. n in methanol (S/C = 500, 50 atm, 25 °C) gave (R)-3a in 99% ee but with only 44% conversion after 48 h. No reaction took place at 8 atm.
20. (a) Delaunay, D.; Le Corre, M. J. Chem. Soc., Perkin Trans. 1 1994, 3041-3042.
21. (b) Matsurnura, Y.; Ohishi, T.; Sonoda, C.; Maki, T.; Watanabe, M. Tetrahedron 1997, 53, 4579-4592.
22. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872-4873.
23. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56 and references therein.
24. (a) Naito, K.; Nagao, T.; Otsuka, M.; Harigaya, S.; Nakajima, H. Jpn. J. Pharmacol. 1985, 38, 235-241.
25. (b) Yokoyama, H.; Yanagisawa, T.; Taira, N. J. Cardiovasc. Pharmacol. 1988, 12, 323-331.
26. (c) Bristiw, M. R.; Hershberger, R. E.; Port, J. D.; Minobe, W.; Rasmussen, R. Mol. Pharmacol. 1989, 35, 295-303 and references therein.
27. Kawaguchi, T.; Saito, K.; Matsuki, K.; Iwakuma, T.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 639-642.
28. Racemic fluoxetin is an antidepressant agent (selective serotonic reuptake inhibitor) developed by Eli Lilly. Its annual sale in 1997 was $2.6 billion. This compound is now in a process of recemic switch. See: Rogers, R. S. Chem. Eng. News 1998, Nov 30, 11-13.
29. Robertson, D. W.; Krushinski, J. H.; Fuller, R. W.; Leander, J. D. J. Med. Chem. 1988, 31, 1412-1417 and references therein.
30. This pretreatment diminishes the induction period and also reduces the amount of strong base in the reaction system, thereby maximizing the efficiency of hydrogenation of the base-sensitive substrate 12.
31. Deeter, J.; Frazier, J.; Staten, G.; Staszak, M.; Weigel, L. Tetrahedron Lett. 1990, 31, 7101-7104.
32. Yevich, J. P.; New, J. S.; Lobeck, W. G.; Dextraze, P.; Bernstein, E.; Taylor, D. P.; Yocca, F. D.; Eison, M. S.; Temple, D. L., Jr. J. Med. Chem. 1992, 35, 4516-4525.
33. For asymmetric reduction of an analogue of 15 with DIP-chloride, see: Ramachandran, P. V.; Gong, B.; Brown, H. C. Chirality 1995, 7, 103-110.
34. Other examples include eprozinol (bronchodilator), isoproterenol (β-adrenoreceptor agonist), proventil (racemate, asthma drug), seldane (racemate, antihistamic agent), and tomoxetine (antidepressant).