Highly efficient asymmetric hydrogenation of alkyl aryl ketones catalyzed by iridium complexes with chiral planar ferrocenyl phosphino-thioether ligands

Advanced Synthesis and Catalysis

Volumn 349, Issue 3, 2007, Pages 309-313

  Le Roux, Erwan ^a   Malacea, Raluca ^b   Manoury, Eric ^b   Poli, Rinaldo ^b   Gonsalvi, Luca ^a   Peruzzini, Maurizio ^a  

^a ICCOM CNR   (Italy)

^b CNRS   (France)

Author keywords

Alkyl aryl ketones; Asymmetric catalysis; Ferrocene ligands; Hydrogenation; Iridium; P,S ligands

Indexed keywords

EID: 34249329662     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600350     Document Type: Article

References (40)

1. a) Comprehensive Asymmetric Catalysis, Vols. 1-3, (Eds.: E. N. Jacobsen, A. Pfalz, H. Yamamoto), Springer, Berlin, 1999;
2. b) Catalytic Asymmetric Synthesis, (Ed.: I. Ojima), Wiley-VCH, New York, 2000.
3. V. Fehring, R. Selke, Angew. Chem. Int. Ed. 1998, 37, 1827.
4. For recent reviews on asymmetric hydrogenation, see: a) H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103;
5. b) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029;
6. c) K. V. L. Crépy, T. Imamoto, Adv. Synth. Catal. 2003, 345, 79.
7. a) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675;
8. b) R. Noyori, T. Ohkuma, Angew. Chem. Int. Ed. 2001, 40, 40;
9. c) R. Noyori, Angew. Chem. Int. Ed. 2002, 41, 2008;
10. d) T. Ohkuma, C. A. Sandoval, R. Srinivasan, Q. Lin, Y. Wie, K. Muniz, R. Noyori, J. Am. Chem. Soc. 2005, 127, 8288.
11. a) M. J. Burk, W. Hems, D. Herzberg, C. Malan, A. Zanotti-Gerosa, Org. Lett. 2000, 2, 4173;
12. b) J. P. Henschke, M. J. Burk, C. J. Malan, D. Herzberg, J. A. Peterson, A. J. Wildsmith, C. J. Cobley, G. Casy, Adv. Synth. Catal. 2003, 345, 300;
13. c) J.-H. Xie, L.-X. Wang, Y. Fu, S.-F. Zhu, B.-M. Fan, H.-F. Duan, Q.-L. Zhou, J. Am. Chem. Soc. 2003, 125, 4404;
14. d) J. Wu, J.-X. Ji, R. Guo, C.-H. Yeung, A. S. C. Chan, Chem. Eur. J. 2003, 9, 2963;
15. e) X. Li, W. Chen, W. Hems, F. King, J. Xiao, Org. Lett. 2003, 5, 4559;
16. f) D. G. Genov, Angew. Chem. Int. Ed. 2004, 43, 2816;
17. g) A. Hu, H. L. Ngo, W. Lin, Org. Lett. 2004, 6, 2937;
18. h) Q. Jing, X. Zhang, J. Sun, K. Ding, Adv. Synth. Catal. 2005, 347, 1193;
19. i) S. Burk, G. Francio, W. Leitner, Chem. Commun. 2005, 3460;
20. j) K. Mikami, K. Wakabayashi, K. Aikawa, Org. Lett. 2006, 8,1517.
21. Cobalt: R. ter Halle, A. Bréhéret, E. Schulz, C. Pinel, M. Lemaire, Tetrahedron: Asymmetry 1997, 8, 2101.
22. Rhodium: a) S. Toros, B. Heil, L. Kollar, L. Marko, J. Organomet. Chem. 1980, 197, 85;
23. b) J. Bakos, I. Toth, B. Heil, G. Szalontai, L. Parkanyi, V. Fülop, J. Organomet. Chem. 1989, 370, 263;
24. c) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. Int. Ed. 1998, 37, 1100;
25. d)Y. Kuroki, Y. Sakamaki, K. Iseki, Org. Lett. 2001, 3, 457.
26. Iridium: a) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318;
27. b) A. Ferrand, M. Bruno, M. L. Tommasino, M. Lemaire, Tetrahedron: Asymmetry 2002, 13, 1379;
28. c) C. Maillet, T. Praveen, P. Janvier, S. Minguet, M. Evain, C. Saluzzo, M. L. Tommasino, B. Bujoli, J. Org. Chem. 2002, 67, 8191;
29. d) L. Dahlenburg, R. Götz, Eur. J. Inorg. Chem. 2004, 888.
30. L Routaboul, S. Vincendeau, J.-C. Daran, E. Manoury, Tetrahedron: Asymmetry 2005, 16, 2685.
31. For the synthesis of enantiomerically pure synthetic intermediates (R)- or (S)-(2-diphenylthiophosphinoferrocenyl)-methanol, see: N. Mateus, L. Routaboul, J.-C. Daran, E. Manoury, J. Organomet. Chem. 2006, 691, 2297.
32. a) R. Malacea, E. Manoury, L. Routaboul, J.-C. Daran, R. Poli, J. P. Dunne, A. C. Withwood, C. Godard, S. B. Duckett, Eur. J. Inorg. Chem. 2006, 1803;
33. b) R Malacea, J.-C. Daran, S. B. Duckett, J. P. Dunne, E. Manoury, R. Poli, A. C. Withwood, Dalton Trans. 2006, 3350.
34. For recent review of halide effects in catalysis, see : K. Fagnou, M. Lautens, Angew. Chem. Int. Ed. 2002, 41, 26.
35. 2 in transition metal-based catalysis, see: a) W.-B. Wang, S.-M. Lu, P.-Y. Yang, X.W. Hen, Y.-G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536;
36. b) Xiao, D.; Zhang, X. Angew. Chem. Int. Ed. 2001, 40, 3425.
37. a) M. Kitamura, S. Okata, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028;
38. b) D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, H. B. Kagan, J. Am. Chem. Soc. 1994, 116, 9430;
39. c) C. Girard, H. B. Kagan, Angew. Chem. Int. Ed. 1998, 37, 2922;
40. d) D. G. Blackmond, Acc. Chem. Res. 2000, 33, 402.