Catalytic asymmetric hydrogenation of pyrimidines

Angewandte Chemie - International Edition

Volumn 54, Issue 8, 2015, Pages 2393-2396

  Kuwano, Ryoichi ^a,b   Hashiguchi, Yuta ^a   Ikeda, Ryuhei ^a   Ishizuka, Kentaro ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Asymmetric catalysis; Heterocycles; Hydrogenation; Iridium; Lanthanides

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; ENANTIOSELECTIVITY; IRIDIUM; ORGANOMETALLICS; RARE EARTH ELEMENTS;

1 ,5-CYCLOOCTADIENE; ASYMMETRIC CATALYSIS; ASYMMETRIC HYDROGENATION; DIPHOSPHINE LIGAND; HETEROCYCLES; HIGH ENANTIOSELECTIVITY; IRIDIUM CATALYST; LANTHANIDE TRIFLATES;

HYDROGENATION;

EID: 85027926634     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410607     Document Type: Article

References (64)

1. a) F. Glorius, Org. Biomol. Chem. 2005, 3, 4171-4175;
2. b) Y.-G. Zhou, Acc. Chem. Res. 2007, 40, 1357-1366;
3. c) R. Kuwano, Heterocycles 2008, 76, 909-922;
4. d) D.-S. Wang, Q.-A. Chen, S.-M. Lu, Y.-G. Zhou, Chem. Rev. 2012, 112, 2557-2590;
5. e) D. Zhao, F. Glorius, Angew. Chem. Int. Ed. 2013, 52, 9616-9618;
6. Angew. Chem. 2013, 125, 9794-9796;
7. f) K. Mashima, T. Nagano, A. Iimuro, K. Yamaji, Y. Kita, Heterocycles 2014, 88, 103-127.
8. a) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. Int. Ed. 2006, 45, 3683-3686;
9. Angew. Chem. 2006, 118, 3765-3768;
10. b) M. Rueping, A. P. Antonchick, Angew. Chem. Int. Ed. 2007, 46, 4562-4565;
11. Angew. Chem. 2007, 119, 4646-4649;
12. c) Q.-A. Chen, D.-S. Wang, Y.-G. Zhou, Y. Duan, H.-J. Fan, Y. Yang, Z. Zhang, J. Am. Chem. Soc. 2011, 133, 6126-6129.
13. a)W.-B. Wang, S.-M. Lu, P.-Y. Yang, X.-W. Han, Y.-G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536-10537;
14. b) D.-W. Wang, X.-B. Wang, D.-S. Wang, S.-M. Lu, Y.-G. Zhou, Y.-X. Li, J. Org. Chem. 2009, 74, 2780-2787;
15. c) W. Tang, Y. Sun, X. Lijin, T. Wang, F. Qinghua, K. H. Lam, A. S. C. Chan, Org. Biomol. Chem. 2010, 8, 3464-3471.
16. L. Shi, Z.-S. Ye, L.-L. Cao, R.-N. Guo, Y. Hu, Y.-G. Zhou, Angew. Chem. Int. Ed. 2012, 51, 8286-8289;
17. Angew. Chem. 2012, 124, 8411-8414.
18. X.-B. Wang, W. Zeng, Y.-G. Zhou, Tetrahedron Lett. 2008, 49, 4922-4924.
19. a) C. Bianchini, P. Barbaro, G. Scapacci, E. Farnetti, M. Graziani, Organometallics 1998, 17, 3308-3310;
20. b)W. Tang, L. Xu, Q.-H. Fan, J. Wang, B. Fan, Z. Zhou, K.-H. Lam, A. S. C. Chan, Angew. Chem. Int. Ed. 2009, 48, 9135-9138;
21. Angew. Chem. 2009, 121, 9299-9302;
22. c) D. Cartigny, T. Nagano, T. Ayad, J.-P. Genêt, T. Ohshima, K. Mashima, V. Ratovelomanana-Vidal, Adv. Synth. Catal. 2010, 352, 1886-1891;
23. d) T. Nagano, A. Iimuro, R. Schwenk, T. Ohshima, Y. Kita, A. Togni, K. Mashima, Chem. Eur. J. 2012, 18, 11578-11592.
24. a) J. Kobayashi, F. Kanda, M. Ishibashi, H. Shigemori, J. Org. Chem. 1991, 56, 4574-4576;
25. b) I. Ohtani, R. E. Moore, M. T. C. Runnegar, J. Am. Chem. Soc. 1992, 114, 7941-7942;
26. c) L. A. McDonald, L. R. Barbieri, G. T. Carter, E. Lenoy, J. Lotvin, P. J. Petersen, M. M. Siegel, G. Singh, R. T.Williamson, J. Am. Chem. Soc. 2002, 124, 10260-10261;
27. d) F. Reyes, R. Fernández, A. Rodríguez, A. Francesch, S. Taboada, C. Ávila, C. Cuevas, Tetrahedron 2008, 64, 5119-5123;
28. e) J. M. Pastor, M. Salvador, M. Argandoña, V. Bernal, M. Reina-Bueno, L. N. Csonka, J. L. Iborra, C. Vargas, J. J. Nieto, M. Cánovas, Biotechnol. Adv. 2010, 28, 782-801.
29. R. Kuwano, N. Kameyama, R. Ikeda, J. Am. Chem. Soc. 2011, 133, 7312-7315.
30. a) R. Kuwano, K. Sato, T. Kurokawa, D. Karube, Y. Ito, J. Am. Chem. Soc. 2000, 122, 7614-7615;
31. b) R. Kuwano, M. Kashiwabara, Org. Lett. 2006, 8, 2653-2655;
32. c) R. Kuwano, M. Kashiwabara, M. Ohsumi, H. Kusano, J. Am. Chem. Soc. 2008, 130, 808-809;
33. d) R. Kuwano, R. Morioka, M. Kashiwabara, N. Kameyama, Angew. Chem. Int. Ed. 2012, 51, 4136-4139;
34. Angew. Chem. 2012, 124, 4212-4215.
35. Z. Yu, W. Jin, Q. Jiang, Angew. Chem. Int. Ed. 2012, 51, 6060-6072;
36. Angew. Chem. 2012, 124, 6164-6177.
37. a) Z.-W. Li, T.-L. Wang, Y.-M. He, Z.-J. Wang, Q.-H. Fan, J. Pan, L.-J. Xu, Org. Lett. 2008, 10, 5265-5268;
38. b) H. Tadaoka,D. Cartigny, T. Nagano, T. Gosavi, T. Ayad, J. P. Genêt, T. Ohshima, V. Ratovelomanana-Vidal, K. Mashima, Chem. Eur. J. 2009, 15, 9990-9994;
39. c) D.-S. Wang, Y.-G. Zhou, Tetrahedron Lett. 2010, 51, 3014-3017;
40. d) A. Iimuro, K. Yamaji, S. Kandula, T. Nagano, Y. Kita, K. Mashima, Angew. Chem. Int. Ed. 2013, 52, 2046-2050;
41. Angew. Chem. 2013, 125, 2100-2104;
42. e) R. N. Guo, X. F. Cai, L. Shi, Z. S. Ye,M.W. Chen, Y. G. Zhou, Chem. Commun. 2013, 49, 8537-8539;
43. f) Y. Kita, A. Iimuro, S. Hida, K. Mashima, Chem. Lett. 2014, 43, 284-286;
44. g) D.-S. Wang, Q.-A. Chen, W. Li, C.-B. Yu, Y.-G. Zhou, X. Zhang, J. Am. Chem. Soc. 2010, 132, 8909-8911;
45. h) D.-S. Wang, Z.-S. Ye, Q.-A. Chen, Y.-G. Zhou, C.-B. Yu, H.-J. Fan, Y. Duan, J. Am. Chem. Soc. 2011, 133, 8866-8869;
46. i) Y. Duan, L. Li, M.-W. Chen, C.-B. Yu, H.-J. Fan, Y.-G. Zhou, J. Am. Chem. Soc. 2014, 136, 7688-7700.
47. a) C. Y. Legault, A. B. Charette, J. Am. Chem. Soc. 2005, 127, 8966-8967;
48. b) S. M. Lu, Y. Q. Wang, X.W. Han, Y. G. Zhou, Angew. Chem. Int. Ed. 2006, 45, 2260-2263;
49. Angew. Chem. 2006, 118, 2318-2321;
50. c) Z.-S. Ye, M.-W. Chen, Q.-A. Chen, L. Shi, Y. Duan, Y.-G. Zhou, Angew. Chem. Int. Ed. 2012, 51, 10181-10184;
51. Angew. Chem. 2012, 124, 10328-10331;
52. d) Z.-S. Ye, R.-N. Guo, X.-F. Cai, M.-W. Chen, L. Shi, Y.-G. Zhou, Angew. Chem. Int. Ed. 2013, 52, 3685-3689;
53. Angew. Chem. 2013, 125, 3773-3777;
54. e) M. Chang, Y. Huang, S. Liu, Y. Chen, S. W. Krska, I. W. Davies, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 12761-12764;
55. Angew. Chem. 2014, 126, 12975-12978.
56. See the Supporting Information.
57. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc. 1994, 116, 4062-4066.
58. 3 suggest that the amidine interacts with the Lewis acid in a solution to form a Yb-2a complex. The ligand exchange of 2a on the Yb center is fast on the NMR timescale. See the Supporting Information.
59. 3. However, the activation with the Brønsted acid is ruled out in this asymmetric hydrogenation. A mixture of some unidentified compounds and remaining 1a (ca. 60%) was obtained when stoichiometric triflic acid was used as the additive in place of the lanthanide triflate under the optimized conditions (at 12 h). The strong acid might cause the ring cleavage of 1a or 3a.
60. a) G. E. Dobereiner, A. Nova, N. D. Schley, N. Hazari, S. J. Miller, O. Eisenstein, R. H. Crabtree, J. Am. Chem. Soc. 2011, 133, 7547-7562;
61. b) R. Dorta,D. Broggini, R. Stoop,H. Ruegger, F. Spindler, A. Togni, Chem. Eur. J. 2004, 10, 267-278;
62. c) D. Xiao, X. Zhang, Angew. Chem. Int. Ed. 2001, 40, 3425-3428;
63. Angew. Chem. 2001, 113, 3533-3536.
64. R. H. Crabtree, M. Lavin, L. Bonneviot, J. Am. Chem. Soc. 1986, 108, 4032-4037.