BINAP/1,4-diamine-ruthenium(II) complexes for efficient asymmetric hydrogenation of 1-tetralones and analogues

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2681-2683

  Ohkuma, Takeshi ^a   Hattori, Tomonori ^a   Ooka, Hirohito ^b   Inoue, Tsutomu ^b   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b NIPPON SODA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; COMBINATORIAL CHEMISTRY; ENANTIOSELECTIVITY; HYDROGENATION; METHYLATION; MOLECULAR DYNAMICS;

EID: 4344593989     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049157c     Document Type: Article

References (30)

1. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73.
2. BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl. TolBINAP = 2,2′-bis(di-4-tolylphosphino)-1,1′-binaphthyl. XylBINAP = 2,2′-bis(di-3,5-xylylphosphino)-1,1′-binaphthyl. DAIPEN = 1,1-di(4-anisyl)-2-isopropyl-1,2-ethylenediamine. DPEN = 1,2- diphenylethylenediamine.
3. (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676.
4. (b) Ohkuma, T.; Doucet, H.; Pham, T.; Mikami, K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086-1087.
5. (c) 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.
6. (d) 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.
7. (e) Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
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11. (a) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417-10418.
12. (b) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468.
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14. Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490-13503. See also: Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104-15118.
15. Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490-13503. See also: Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104-15118.
16. Asymmetric hydrogenation of 1a, giving 2a in 95% ee and 88% yield, was achieved with a BINAP-Ir complex with an achiral amino phosphine under harsh conditions and with a rather high catalyst loading (50-57 atm, 90°C, 75 h, S/C = 190-230). Zhang, H.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318-3319.
17. 3N mixture gave 2a in 99% ee and quantitatively but only with S/C = 200. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
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22. Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1-13.
23. A single recrystallization from a 1:3 mixture of methanol and hexane at -30°C gave pure (R)-2b in 81%.
24. (a) Tombo, G. M. R.; Bellus, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1193-1215.
25. (b) Keith, R. A.; Warawa, E. J.; Simpson, T. R. PCT Int. Appl. WO 9932461, 1999.
26. 4)(diphosphine)(1,2-diamine) complex, see refs 6 and 7.
27. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
28. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872-4873.
29. 5b
30. 5b