The development of double axially chiral phosphoric acids and their catalytic transfer hydrogenation of quinolines

Angewandte Chemie - International Edition

Volumn 47, Issue 4, 2008, Pages 759-762

  Guo, Qun Sheng ^a   Du, Da Ming ^a   Xu, Jiaxi ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Asymmetric synthesis; Br nsted acid; Hydrogenation; Organocatalysis; Tetrahydroquinolines

Indexed keywords

ENANTIOSELECTIVITY; HYDROGENATION; PHOSPHORIC ACID;

ASYMMETRIC SYNTHESIS; BRØNSTED ACID; ORGANOCATALYSIS; TETRAHYDROQUINOLINES;

CATALYST ACTIVITY;

PHOSPHORIC ACID; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HYDROGENATION; MOLECULAR CONFORMATION; PHOSPHORIC ACIDS; QUINOLINES; STEREOISOMERISM;

EID: 38349018738     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703925     Document Type: Article

References (52)

1. Comprehensive Asymmetric Synthesis, Vols. I, II, and III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
2. a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592;
3. Angew. Chem. Int. Ed. 2004, 43, 1566;
4. b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
5. c) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804.
6. For recent reviews on the use of chiral Brønsted acids as catalysts, see a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
7. b) P. M. Pihko, Angew. Chem. 2004, 116, 2110;
8. Angew. Chem. Int. Ed. 2004, 43, 2062;
9. c) C. Bolm, T. Rantanen, I. Schiffers, L. Zani, Angew. Chem. 2005, 117, 1788;
10. Angew. Chem. Int. Ed. 2005, 44, 1758;
11. d) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550;
12. Angew. Chem. Int. Ed. 2006, 45, 1520;
13. e) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999;
14. f) S. J. Connon, Angew. Chem. 2006, 118, 4013;
15. Angew. Chem. Int. Ed. 2006, 45, 3909.
16. a) M. Rueping, E. Sugiono, E. Azap, T. Theissmann, M. Beller, Org. Lett. 2005, 7, 3781;
17. b) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84;
18. c) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086;
19. d) Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484;
20. e) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070;
21. f) N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368;
22. g) M. Rueping, A. P. Antonchick, Angew. Chem. 2007, 119, 4646;
23. Angew. Chem. Int. Ed. 2007, 46, 4562;
24. h) M. Terada, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 292;
25. i) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756;
26. j) J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498.
27. a) H. Liu, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Org. Lett. 2006, 8, 6023;
28. b) X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 2006, 128, 14802;
29. c) Q.-X. Guo, H. Liu, C. Guo, S.-W. Luo, Y. Gu, L.-Z. Gong, J. Am. Chem. Soc. 2007, 129, 3790;
30. d) M. Rueping, E. Sugiono, T. Theissmann, A. Kuenkel, A. Köckritz, A. Pews-Davtyan, N. Nemati, M. Beller, Org. Lett. 2007, 9, 1065.
31. a) T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 2005, 347, 1523;
32. b) M. R. Nahm, J. R. Potnick, P. S. White, J. S. Johnson, J. Am. Chem. Soc. 2006, 128, 2751.
33. a) G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830;
34. b) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696.
35. For details see the Supporting Information.
36. For selected reviews, see a) R. Noyori, Angew. Chem. 2002, 114, 2108;
37. Angew. Chem. Int. Ed. 2002, 41, 2008;
38. b) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029;
39. c) F. Glorius, Org. Biomol. Chem. 2005, 3, 4171;
40. d) Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley, New York, 2000;
41. e) Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
42. f) Principles and Applications of Asymmetric Synthesis (Eds.: G.-Q. Lin, Y.-M. Li, A. S. C. Chan), John Wiley & Sons, New York, 2001;
43. for selected examples, see g) C. Y. Legault, A. B. Charette, J. Am. Chem. Soc. 2005, 127, 8966;
44. h) R. Kuwano, M. Kashiwabara, Org. Lett. 2006, 8, 2653;
45. i) S.-M. Lu, Y.-Q. Wang, X.-W. Han, Y.-G. Zhou, Angew. Chem. 2006, 118, 2318;
46. Angew. Chem. Int. Ed. 2006, 45, 2260.
47. For selected recent examples, see a) W.-B. Wang, S.-M. Lu, P.-Y. Yang, X.-W. Han, Y.-G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536;
48. b) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765;
49. Angew. Chem. Int. Ed. 2006, 45, 3683;
50. c) K. H. Lam, J. Ji, J. Wu, Q.-H. Fan, W.-H. Lo, A. S. C. Chan, Chem. Commun. 2005, 1390;
51. d) Z.-J. Wang, G.-J. Deng, Y. Li, Y.-M. He, W.-J. Tang, Q.-H. Fan, Org. Lett. 2007, 9, 1243;
52. e) W.-J. Tang, S.-F. Zhou, L.-J. Xu, Q.-L. Zhou, Q.-H. Fan, H. F. Zhou, K. Lam, A. S. C. Chan, Chem. Commun. 2007, 613.