Discrimination of β-ketoesters by ruthenium(II)-binap-catalyzed asymmetric hydrogenation

Angewandte Chemie - International Edition

Volumn 46, Issue 34, 2007, Pages 6537-6541

  Kramer, Rainer ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

ketoesters; Asymmetric catalysis; Kinetics; Reduction; Substituent effects

Indexed keywords

ALKALINITY; CATALYSIS; KETONES; REDUCTION; RUTHENIUM COMPOUNDS; SUBSTITUTION REACTIONS;

ASYMMETRIC CATALYSIS; KETOESTERS; LEWIS BASICITY; SUBSTITUENT EFFECTS;

ESTERS;

EID: 34548301131     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700021     Document Type: Article

References (75)

1. a) R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856-5858;
2. b) M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, R. Noyori, J. Am. Chem. Soc. 1988, 110, 629-631;
3. c) R. Noyori, Science 1990, 248, 1194-1199.
4. For reviews, see: a) R. Noyori, Angew. Chem. 2002, 114, 2108-2123;
5. Angew. Chem. Int. Ed. 2002, 41, 2008-2022;
6. b) T. Ohkuma, M. Kitamura, R. Noyori in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), 2nd ed., Wiley-VCH, Weinheim, 2000, pp. 1-111;
7. c) T. Ohkuma, R. Noyori in Comprehensive Asymmetric Catalysis I (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 199-245;
8. d) D. J. Ager, S. A. Laneman, Tetrahedron: Asymmetry 1997, 8, 3327-3355.
9. a) V. A. Pavlov, Usp. Khim. 2001, 70, 1175-1205,
10. Russ. Chem. Rev. 2001, 70, 1037-1065;
11. b) J.-P. Genêt, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, L. Bischoff, M. C. Cano De Andrade, S. Darses, C. Galopin, J. A. Lafitte, Tetrahedron: Asymmetry 1994, 5, 675-690.
12. R. Birk, M. Karpf, K. Pünterer, M. Scalone, M. Schwindt, U. Zutter, Chimia 2006, 60, 561-565.
13. T. Saito, T. Yokozawa, K. Matsumura, N. Sayo (Takasago Int. Corp.), US Patent 6,492,545 B2, 2002.
14. For the asymmetric reduction of several tons of methyl acetoacetate, see: H. Kumobayashi, Recl. Trav. Chim. Pays-Bas 1996, 115, 201-210.
15. a) M. Kitamura, T. Ohkuma, H. Takaya, R. Noyori, Tetrahedron Lett. 1988, 29, 1555-1556;
16. b) M. Kitamura, M. Tokunaga, T. Ohkuma, R. Noyori, Tetrahedron Lett. 1991, 32, 4163-4166.
17. For an overview until 2000, see Ref. [2]; for recent reports, see: a) L. Chai, H. Chen, Z. Li, Q. Wang, F. Tao, Synlett 2006, 2395-2398;
18. b) L. Qiu, F. Y. Kwong, J. Wu, W. H. Lam, S. Chan, W.-Y. Yu, Y.-M. Li, R. Guo, Z. Zhou, A. S. C. Chan, J. Am. Chem. Soc. 2006, 128, 5955-5965;
19. c) Y.-Y. Huang, Y.-M. He, H.-F. Zhou, L. Wu, B.-L. Li, Q.-H. Fan, J. Org. Chem. 2006, 71, 2874-2877;
20. d) C.-J. Wang, H. Tao, X. Zhang, Tetrahedron Lett. 2006, 47, 1901-1903;
21. e) X. Wang, Y. Sun, Y. Luo, D. Li, Z. Zhang, J. Org. Chem. 2005, 70, 1070-1072;
22. f) A. Hu, H. L. Ngo, W. Lin, Angew. Chem. 2004, 116, 2555-2558;
23. Angew. Chem. Int. Ed. 2004, 43, 2501-2504;
24. g) S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, Angew. Chem. 2004, 116, 324-329;
25. Angew. Chem. Int. Ed. 2004, 43, 320-325;
26. h) M. Berthod, C. Saluzzo, G. Mignani, M. Lemaire, Tetrahedron: Asymmetry 2004, 15, 639-645;
27. i) S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, Proc. Natl. Acad. Sci. USA 2004, 101, 5799-5804;
28. j) C. Mordant, P. Dünkelmann, V. Ratovelomanana-Vidal, J.-P. Genêt, Chem. Commun. 2004, 1296-1297;
29. k) S. Duprat de Paule, S. Jeulin, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, Eur. J. Org. Chem. 2003, 1931-1941;
30. l) J.-P. Genêt, Acc. Chem. Res. 2003, 36, 908-918;
31. m) H. L. Ngo, A. Hu, W. Lin, Chem. Commun. 2003, 1912-1913;
32. n) S. Duprat de Paule, S. Jeulin, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, Tetrahedron Lett. 2003, 44, 823-826;
33. o) Y.-G. Zhou, W. Tang, W.-B. Wang, W. Li, X. Zhang, J. Am. Chem. Soc. 2002, 124, 4952-4953;
34. p) C.-C. Pai, Y.-M. Li, Z.-Y. Zhou, A. C. S. Chan, Tetrahedron Lett. 2002, 43, 2789-2792;
35. q) J.-P. Genêt, Pure Appl. Chem. 2002, 74, 77-83;
36. r) P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genêt, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426;
37. s) J.-P. Genêt, Pure Appl. Chem. 2001, 73, 299-303;
38. t) T. Saito, T. Yokozawa, T. Ishizaki, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264-267.
39. [17], dowex-50 resin: D. F. Taber, L. Silverberg, Tetrahedron Lett. 1991, 32, 4227-4230;
40. 2]: M. Kitamura, M. Tokunaga, T. Ohkuma, R. Noyori, Org. Synth. 1992, 71, 1-13;
41. [17], HCl: S. A. King, A. S. Thompson, A. O. King, T. R. Verhoeven, J. Org. Chem. 1992, 57, 6689-6691;
42. 2] (cod = 1,5-cyclooctadiene), HBr: J.-P. Genêt, V. Ratovelomanana-Vidal, M. C. Cano de Andrade, X. Pfister, P. Guerreiro, J. Y. Lenoir, Tetrahedron Lett. 1995, 36, 4801-4804;
43. 3, (S)- MeO-biphep (biphep = 2,2′-bis(diphenylphosphanyl)biphenyl): J. Madec, P. Phansavath, V. Ratovelomanana-Vidal, J.-P. Genêt, Tetrahedron 2001, 57, 2563-2568;
44. 2(diphosphane)]: V. Ratovelomanana-Vidal, C. Girard, R. Touti, J. P. Tranchier, B. Ben Hassine, J.-P. Genêt, Adv. Synth. Catal. 2003, 345, 261-274.
45. For an overview until 2000, see Ref. [2]; for more recent reports, see: a) A. Fürstner, M. D. B. Fenster, B. Fasching, C. Godbout, K. Radkowski, Angew. Chem. 2006, 118, 5632-5636;
46. Angew. Chem. Int. Ed. 2006, 45, 5506-5510;
47. b) L.-S. Deng, X.-P. Huang, G. Zhao, J. Org. Chem. 2006, 71, 4625-4635;
48. c) N. Desroy, R. L. Roux, P. Phansavath, L. Chiummiento, C. Bonini, J.-P. Genêt, Tetrahedron Lett. 2003, 44, 1763-1766;
49. d) C. Herb, M. E. Maier, J. Org. Chem. 2003, 68, 8129-8135;
50. e) C. Aissa, R. Riveiros, J. Ragot, A. Fürstner, J. Am. Chem. Soc. 2003, 125, 15512-15520;
51. f) A. Fürstner, M. Albert, J. Mlynarski, M. Mathieu, E. Declerq, J. Am. Chem. Soc. 2003, 125, 13132-13142;
52. g) E. B. Holson, W. R. Roush, Org. Lett. 2002, 4, 3719-3722;
53. h) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5286-5298;
54. i) S. Hoppen, S. Bäurle, U. Koert, Chem. Eur. J. 2000, 6, 2382-2396;
55. j) A. Fürstner, O. R. Thiel, G. Blanda, Org. Lett. 2000, 2, 3731-3734.
56. Very recently, the first AH reactions of unsymmetrical bis(β-ketoesters) were described: P. A. Wender, J. C. Horan, Org. Lett. 2006, 8, 4581-4584;
57. P. A. Wender, J. C. Horan, V. A. Verma, Org. Lett. 2006, 8, 5299-5302.
58. However, both β-ketoester moieties in each of the two reported substrates were reduced. Two symmetric bis(β-ketoester)s were reduced asymmetrically at both termini with relatively little enantioselectivity: J. Kiegil, J. Jóźwik, K. Wózniak, J. Jurczak, Tetrahedron Lett. 2000, 41, 4959-4963.
59. For methods for the synthesis of β-ketoesters, see: S. Benetti, R. Romagnoli, Chem. Rev. 1995, 95, 1065-1114.
60. See the Supporting Information for the preparation of β-ketoesters 5a-d.
61. 13C NMR spectra of which were not recorded, as the compounds exist as keto/enol mixtures), and correct combustion analytical data were obtained for all new compounds (except 5d, 6c, 6d, for which only HRMS data were obtained).
62. R. Kramer, R. Brückner, Chem. Eur. J., DOI: 10.1002/chem.200700527.
63. For the first preparation of this complex, see: S. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S. Yoshikawa, S. Akutagawa, J. Chem. Soc. Chem. Commun. 1985, 922-924.
64. - (L. DiMichele, S. A. King, A. W. Douglas, Tetrahedron: Asymmetry Tetrahedron Asym. 2003, 14, 3427-3430),
65. - (T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, M. Mashima, Organometallics 1996, 15, 1521-1523)
66. - (K. Mashima, T. Nakamura, Y. Matsuo, K. Tani, J. Organomet. Chem. 2000, 607, 51-56).
67. [9c] 75%).
68. [17] for the AH of a β-ketoester, see Ref. [1a].
69. See Ref. [9a,c]; a) D. F. Taber, P. B. Deker, L. J. Silverberg, J. Org. Chem. 1992, 57, 5990-5994;
70. b) D. F. Taber, Y. Wang, J. Am. Chem. Soc. 1997, 119, 22-26;
71. 2((S)-binap)(p-cymene)], see: A. Wolfson, I. F. J. Vankelecom, S. Geresh, P. A. Jacobs, J. Mol. Catal. A 2004, 217, 21-26.
72. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
73. R(R enantiomer) = 166.2 min.
74. GC analysis on an achiral phase was performed with a Carlo Erba Instruments ICU 600 GC 6000 Vega Series apparatus with a dimethylpolysiloxane column (J&W Scientific, SE-30, 25 m x 0.33 mm). Details of temperature and time are specified in the captions of Figures 2-5).
75. Ethanolysis of β-ketoesters 5b-d during GC analysis (a) and in separate deliberate experiments (b): a) Heat (250°C) in the injection chamber of the GC apparatus; incomplete conversions of 5b and c, complete conversion of 5d; b) EtOH, reflux, 1 h; 11: trace, 12: 91%. An authentic specimen of ethyl ester 10 was prepared by a crossed Claisen condensation (75% yield). (Chemical Equation Presented)