Ruthenium-catalysed asymmetric reduction of ketones

Platinum Metals Review

Volumn 49, Issue 4, 2005, Pages 158-165

  Zanotti Gerosa, Antonio ^a,b   Hems, William ^a,c   Groarke, Michelle ^a,c   Hancock, Fred ^a,c  

^a JOHNSON MATTHEY TECHNOLOGY CENTRE   (United Kingdom)

^b Johnson Matthey's Catalysis and Chiral Technologies (CCT)   (United States)

^c Johnson Matthey CCT ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC REDUCTION; SECONDARY ALCOHOLS; SYNTHETIC CHEMISTRY; TYRANSFER HYDROGENATION;

CATALYSIS; CATALYSTS; HYDROGENATION; REDUCTION; RUTHENIUM; STEREOCHEMISTRY;

KETONES;

EID: 27744433940     PISSN: 14710676     EISSN: 14710676     Source Type: Journal    
DOI: 10.1595/147106705X75421     Document Type: Review

References (39)

1. T. Ohkuma and R. Noyori, in "Comprehensive Asymmetric Catalysis", eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin, 1999, Vol. I, and 2004, Supplement I
2. H. U. Blaser, F. Spindler and M. Studer, Appl. Catal. A: Gen., 2001, 221, 119
3. (a) R. Noyori, "Nobel Lecture', Angew. Chem. Int. Ed., 2002, 41, 2008;
4. (b) R. Noyori, M. Kitamura and T. Ohkuma, Prof. Natl. Acad. Sci., 2004, 101, 5356
5. (a) H. Doucet, T, Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T. Ikariya and R. Noyori, Angew. Chem. Int. Ed., 1998, 37, 1703;
6. (b) for a review see: R. Noyori and T. Ohkuma, Angew. Chem. Int. Ed., 2001, 40, 40
7. C. A. Sandoval, T. Ohkuma, K. Muniz and R. Noyori, J. Am. Chem. Soc., 2003, 125, 13490
8. The so-called 3,5-di-meta alkyl effect is also known in other catalytic reactions: P. Dotta, A. Magistrato, U. Rothlisberger, P. S. Pregosin and A. Albinati, Organometallics, 2002, 21, 3033
9. A. Hu, H. L. Ngo and W. Lin, Org. Lett., 2004, 6, 2937
10. (a) J. Wu, H. Chen, W. Kwok, R. Guo, Z. Zhou, C. Yeung and A. S. C. Chan, J. Org. Chem., 2002, 67, 7908;
11. (b) J. Wu, J-X. Ji, R. Guo, C-H. Yeung and A. S. C. Chan, Eur. J. Chem., 2003, 9, 2963
12. P. J. Pye, K. Rossen, R. A. Reamer, N. N. Tsou, R. P. Volante and P. J. Reider, J. Am. Chem. Soc., 1997, 119, 6207
13. (a) M. J. Burk, W. Hems, D. Herzberg, C. Malan and A. Zanotri-Gerosa, Org. Lett., 2000, 2, 4173;
14. (b) D. Chaplin, P. Harrison, J. Henschke, I. Lennon, G. Meek, P. Moran, C. J. Pilkington, J. A. Ramsden, S. Watkins and A. Zanotri-Gerosa, Org. Process Res. Dev., 2003, 7, 89
15. B. Dominguez, A. Zanotti-Gerosa and W. Hems, Org. Lett., 2004, 6, 1927
16. D. G. Genov and D. J. Ager, Angew. Chem. Int. Ed., 2004, 43, 2816
17. K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto and S. Matsukawa, Acc. Chem. Res., 2000, 33, 391
18. T. Ohkuma, T. Hattori, H. Ooka, T. Inoue and R. Noyori, Org. Lett., 2004, 6, 2681
19. G. A. Grasa, A. Zanotti-Gerosa, J. A. Medlock and W. P. Hems, Org. Lett., 2005, 7, 1449
20. (a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 2521;
21. (b) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya and R. Noyori. J. Am. Chem. Soc., 1996, 118, 4916;
22. (c) S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya and R. Noyori, Angew. Chem. Int. Ed., 1997, 36, 288;
23. (d) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya and R. Noyori, Angew. Chem. Int. Ed., 1997, 36, 285
24. R. Noyori, M. Yamakawa and S. Hashiguchi, J. Org. Chem., 2001, 66, 7931
25. T. Koike and T. Ikariya, Adv. Synth. Catal., 2004, 346, 37
26. (a) D. Sterk, M. S. Stephan and B. Mohar, Tetrahedron: Asymmetry, 2002, 13, 2605;
27. (b) D. Sterk, M. S. Stephan and B. Mohar, Tetrahedron Lett., 2004, 45, 535
28. Y. Ma, H. Liu, L. Chen, X. Cui, J. Zhu and J. Deng, Org. Lett., 2003, 12, 2103
29. X. Wu, X. Li, W. Hems, F. King and J. Xiao, Org. Biomol. Chem., 2004, 2, 1818
30. M. Watanabe, K. Murata and T. Ikariya, J. Org. Chem., 2002, 67, 1712
31. (a) K. Okano, K. Murata and T. Ikariya, Tetrahedron Lett., 2000, 41, 9277;
32. (b) I. C. Lennon and J. A. Ramsden, Org. Proc. Res. Dev., 2005, 9, 110
33. (a) K. Everaere, N. Franceschini, A. Montreux and J.-F. Carpentier, Tetrahedron Lett., 2002, 43, 2569;
34. (b) F. Eustache, P. I. Dalko and J. Cossy, Org. Lett., 2002, 4, 1263
35. T. Koike, K. Murata and T. Ikariya, Org. Lett., 2000, 2, 3833
36. (a) K. Tanaka, M. Katsurada, F. Ohno, Y. Shiga, M. Oda, M. Miyagi, J. Takehara and K. Okano, J. Org. Chem., 2000, 65, 432;
37. (b) M. Miyagi, J. Takehara, S. Collet and K. Okano, Org. Proc. Res. Dev., 2000, 4, 346
38. T. Ohkuma, M. Koizumi, K. Muniz, G. Hilt, C. Kabuto and R. Noyori, J. Am. Chem. Soc., 2002, 124, 6508
39. M. Scalone and P. Waldmeier, Org. Process. Res. Dev., 2003, 7, 418