Asymmetric hydrogenation of aromatic ketones catalyzed by the TolBINAP/DMAPEN-ruthenium(II) complex: A significant effect of N-substituents of chiral 1,2-diamine ligands on enantioselectivity

Journal of Organic Chemistry

Volumn 73, Issue 22, 2008, Pages 9084-9093

  Ooka, Hirohito ^a   Arai, Noriyoshi ^a   Azuma, Keita ^a   Kurono, Nobuhito ^a   Ohkuma, Takeshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CATALYSTS; CHEMICAL REACTIONS; COORDINATION REACTIONS; ELECTRON TRANSITIONS; ETHERS; HYDROGENATION; KETONES; LIGANDS; ORGANIC COMPOUNDS; RUTHENIUM; RUTHENIUM ALLOYS; RUTHENIUM COMPOUNDS;

ACETOPHENONE; AROMATIC KETONES; ARYL KETONES; ASYMMETRIC HYDROGENATIONS; CATALYST PRECURSORS; CHEMICAL EQUATIONS; CHIRAL ALCOHOLS; CHIRAL CATALYSTS; DI-AMINES; DIAMINE LIGANDS; DYNAMIC KINETIC RESOLUTIONS; METHYL ETHERS; RU COMPLEXES; RUTHENIUM COMPLEXES; SUBSTITUENT EFFECTS; TRANSITION STATE MODELS; X-RAY STRUCTURES;

ENANTIOSELECTIVITY;

ACETAL; ACETOPHENONE; ALCOHOL; DIMETHYL ETHER; PHENETHYLAMINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; HYDROGENATION; MATHEMATICAL MODEL;

EID: 56449085763     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801863q     Document Type: Article

References (56)

1. (a) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin-Heidelberg, Germany, 1999; Vol. 1, pp 199-246.
2. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110.
3. (c) Ohkuma, T.; Noyori, R. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, pp 29-113.
4. (d) Ohkuma, T.; Noyori, R. In The Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; Vol. 3, pp 1105-1163.
5. (a) Ohkuma, T. J. Synth. Org. Chem. Jpn. 2007, 65, 1070-1080.
6. (b) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73.
7. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676.
8. 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.
9. XylBINAP = 2,2′-bis(di-3,5-xylylphosphino)-1,1′-binaphthyl. DAIPEN = 1,1-di(4-anisyl)-2-isopropyl-1,2-ethylenediamine.
10. 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.
11. Ohkuma, T.; Koizumi, M.; Muñiz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508-6509.
12. Ohkuma, T.; Hattori, T.; Ooka, H.; Inoue, T.; Noyori, R. Org. Lett. 2004, 6, 2681-2683.
13. Ohkuma, T.; Sandoval, C. A.; Srinivasan, R.; Lin, Q.; Wei, Y.; Muniz, K.; Noyori, R. J. Am. Chem. Soc. 2005, 127, 8288-8289.
14. Arai, N.; Suzuki, K.; Sugizaki, S.; Sorimachi, H.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 1770-1773.
15. (a) Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490-13503.
16. (b) Noyori, R.; Sandoval, C. A.; Muñiz, K.; Ohkuma, T. Phil. Trans. R. Soc. A 2005, 363, 901-912.
17. (a) Abdur-Rashid, K.; Faatz, M.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2001, 123, 7473-7474.
18. (b) 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.
19. (c) Hamilton, R. J.; Leong, C. G.; Bigam, G.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2005, 127, 4152-4153.
20. (d) Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2006, 128, 13700-13701.
21. (e) Leyssens, T.; Peeters, D.; Harvey, J. N. Organometallics 2008, 27, 1514-1523.
22. For the (S)-TolBINAP-Ru chelate structure, see the ORTEP drawing in Figure 2. See also ref 4.
23. (a) Oki, M.; Mutai, K. Bull. Chem. Soc. Jpn. 1960, 33, 784-789.
24. (b) Oki, M.; Mutai, K. Bull. Chem. Soc. Jpn. 1965, 38, 387-392.
25. (c) Oki, M.; Mutai, K. Bull. Chem. Soc. Jpn. 1966, 39, 809-813.
26. For ammonium/π(aryl) interaction, see: (a) Meot-Ner, M.; Deakyne, C. A. J. Am. Chem. Soc. 1985, 107, 469-474.
27. (b) Singh, J.; Thornton, J. M. J. Mol. Biol. 1990, 211, 595-615.
28. (c) Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558-1560.
29. (d) Garel, L.; Lozach, B.; Dutasta, J.-P.; Collet, A. J. Am. Chem. Soc. 1993, 115, 11652-11653.
30. (e) Koh, K. N.; Araki, K.; Ikeda, A.; Otsuka, H.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 755-758.
31. (f) Roelens, S.; Torriti, R. J. Am. Chem. Soc. 1998, 120, 12443-12452.
32. (g) Gallivan, J. P.; Dougherty, D. A. Proc Natl. Acad. Sci. U.S.A. 1999, 96, 9459-9464.
33. DFT calculations of transition states in asymmetric hydrogenation of la with the TolBINAP/DPEN-Ru(II) catalyst also suggested the presence of an NH/π interaction, see: (a) French, S. A.; Di Tommaso, D.; Zanotti-Gerosa, A.; Hancock, F.; Catlow, C. R. A. Chem. Commun. 2007, 2381-2388.
34. (b) Di Tommaso, D.; French, S. A.; Zanotti-Gerosa, A.; Hancock, F.; Palin, E. J.; Catlow, C. R. A. Inorg. Chem. 2008, 47, 2674-2687.
35. A preliminary communication, see: Arai, N.; Ooka, H.; Azuma, K.; Yabuuchi, T.; Kurono, N.; Inoue, T.; Ohkuma, T. Org. Lett. 2007, 9, 939-941.
36. Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1-13.
37. 2[(5)-tolbinap][(S,S)-dpen] has two d-chelate structures with both ligands. See ref 4.
38. Nieduzak, T. R.; Margolin, A. L. Tetrahedron: Asymmetry 1991, 2, 113-122.
39. 3 catalysts modified by cinchonidine derivatives gave the alcohols in 81% and 89% ee, respectively, see: Studer, M.; Burkhardt, S.; Blaser, H.-U. Chem. Commun. 1999, 1727-1728.
40. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
41. (a) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872-4873.
42. (b) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510-6511.
43. (c) Ohkuma, T.; Li, J.; Noyori, R. Synlett 2004, 1383-1386.
44. 3N mixture selectively gave the syn alcohol. See: Murata, K.; Okano, K.; Miyagi, M.; lwane, H.; Noyori, R.; Ikariya, T. Org. Lett. 1999, 1, 1119-1121.
45. Hughes, D. T. D.; Empey, D. W.; Land, M. J. Clin. Hosp. Pharm. 1983, 8, 315-321.
46. Myers, A. G.; Charest, M. G. In Handbook of Reagents for Organic Synthesis: Chiral Reagents for Asymmetric Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, UK, 2003; pp 485-496, and references cited therein.
47. (a) Meseras, F.; Lledós, A.; Clot, E.; Eisenstein, O. Chem. Rev. 2000, 100, 601-636.
48. (b) Kubas, G. J. J. Organomet. Chem. 2001, 635, 37-68.
49. Repulsive interaction between the filled p and d orbitals has also been postulated: Caulton, K. G. New J. Chem. 1994, 18, 25-41.
50. ax in the transition state, see ref 12e.
51. (a) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
52. (b) Anh, N. T. Top. Curr. Chem. 1980, 88, 145-162.
53. Reduction of 9a with potassium tri-sec-butylborohydride (K-Selectride), a bulky and nonchelation reducing agent, in ether at -78°C predominantly afforded anti-10a. See: Davis, F. A.; Haque, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021-2024.
54. See for example: Davis, A. P. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, I., Shaumann, E., Eds.; Thieme: Stuttgart, Germany, 1995; Vol. E21d, pp 3988-4048.
55. (a) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1994, 5, 1147-1150.
56. (b) Cho, B. T.; Chun, Y. S. J. Chem. Soc., Perkin Trans. 1 1999, 2095-2100.