Recent developments in asymmetric transfer hydrogenation with hantzsch esters: A biomimetic approach

Chemistry - An Asian Journal

Volumn 2, Issue 7, 2007, Pages 820-827

  You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Hantzsch esters; Hydrogenation; Organocatalysis; Reductive amination

Indexed keywords

ESTER; HYDROGEN;

ARTICLE; CATALYSIS; CHEMISTRY; MOLECULAR MIMICRY; STEREOISOMERISM;

CATALYSIS; ESTERS; HYDROGEN; MOLECULAR MIMICRY; STEREOISOMERISM;

EID: 34447306019     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700081     Document Type: Article

References (82)

1. For reviews, see: a) Asymmetric Catalysis in Organic Synthesis (Ed.: R. Noyori), Wiley, New York, 1994;
2. b) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, Weinheim, 1999;
3. c) Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
4. d) G-Q. Lin, Y-M. Li, A. S. C. Chan, Principles and Applications of Asymmetric Synthesis, John Wiley & Sons, New York, 2001.
5. a) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069;
6. b) H. U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103-151;
7. c) X. Cui, K. Burgess, Chem. Rev. 2005, 105, 3272-3297;
8. d) C. Jaekel, R. Paciello, Chem. Rev. 2006, 106, 2912-2942;
9. e) S. Gladiali, E. Alberico, Chem. Soc. Rev. 2006, 35, 226-236.
10. a) W. S. Knowles, Angew. Chem. 2002, 114, 2096-2107;
11. Angew. Chem. Int. Ed. 2002, 41, 1998-2007;
12. b) R. Noyori, Angew. Chem. 2002, 114, 2108-2123;
13. Angew. Chem. Int. Ed. 2002, 41, 2008-2022.
14. Recent examples of highly enantioselective reduction of C=C bonds: a) S. Bell, B. Wüstenberg, S. Kaiser, F. Menges, T. Netscher, A. Pfaltz, Science 2006, 311, 642-644;
15. b) C. Hedberg, K. Källström, P. Brandt, L. K. Hansen, P. G. Andersson, J. Am. Chem. Soc. 2006, 128, 2995-3001;
16. c) M. Weis, C. Waloch, W. Seiche, B. Breit, J. Am. Chem. Soc. 2006, 128, 4188-4189;
17. d) M. T. Reetz, Y. Fu, A. Meiswinkel, Angew. Chem. 2006, 118, 1440-1443;
18. Angew. Chem. Int. Ed. 2006, 45, 1412-1415;
19. e) L. Shi, X. Wang, C. A. Sandoval, M. Li, Q. Qi, Z. Li, K. Ding, Angew. Chem. 2006, 118, 4214-4218;
20. Angew. Chem. Int. Ed. 2006, 45, 4108-4112;
21. f) S. Kaiser, S. P. Smidt, A. Pfaltz, Angew. Chem. 2006, 118, 5318-5321;
22. Angew. Chem. Int. Ed. 2006, 45, 5194-5197;
23. g) G.-H. Hou, J.-H. Xie, L.-X. Wang, Q.-L. Zhou, J. Am. Chem. Soc. 2006, 128, 11 774-11 775;
24. h) Y. Liu, C. A. Sandoval, Y. Yamaguchi, X. Zhang, Z. Wang, K. Kato, K. Ding, J. Am. Chem. Soc. 2006, 128, 14 212-14 213.
25. C=N bonds: a) C. Moessner, C. Bolm, Angew. Chem. 2005, 117, 7736-7739;
26. Angew. Chem. Int. Ed. 2005, 44, 7564-7567;
27. b) Q. Yang, G. Shang, W. Gao, J. Deng, X. Zhang, Angew. Chem. 2006, 118, 3916-3919;
28. Angew. Chem. Int. Ed. 2006, 45, 3832-3835;
29. c) G. Shang, Q. Yang, X. Zhang, Angew. Chem. 2006, 118, 6508-6510;
30. Angew. Chem. Int. Ed. 2006, 45, 6360-6362;
31. d) S.-F. Zhu, J.-B. Xie, Y.-Z. Zhang, S. Li, Q.-L. Zhou, J., Am. Chem. Soc. 2006, 128, 12 886-12 891.
32. C=O bonds: a) M. T. Reetz, X. Li, J. Am. Chem. Soc. 2006, 128, 2044-2045;
33. b) H. Huang, T. Okuno, K. Tsuda, M. Yoshimura, M. Kitamura, J. Am. Chem. Soc. 2006, 128, 8716-8717;
34. c) T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C. Sandoval, R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724-8725.
35. Quinolines and isoquinolines: a) S.-M. Lu, Y.-Q. Wang, X.-W. Han, Y.-G. Zhou, Angew. Chem. 2006, 118, 2318-2321;
36. Angew. Chem. Int. Ed. 2006, 45, 2260-2263; multiple-hydrogenation process:
37. 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, and references therein.
38. a) B. Alberts, D. Bray, J. Lewis, M. Raff, K. Roberts, J. D. Watson, Molecular Biology of the Cell. 3rd ed., Garland, New York, 2002;
39. b) J. M. Berg, J. L. Tymoczko, L. Stryer, Biochemistry, 5th ed., W. H. Freeman & Company, New York, 2002.
40. a) J. W. Yang, M. T. Hechavarria Fonseca, B. List, Angew. Chem. 2004, 116, 6829-6832;
41. Angew. Chem. Int. Ed. 2004, 43, 6660-6662;
42. b) J. W. Yang, M. T. Hechavarria Fonseca, N. Vignola, B. List, Angew. Chem. 2005, 117, 110-112;
43. Angew. Chem. Int. Ed. 2005, 44, 108-110;
44. c) J. W. Yang, M. T. Hechavarria Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15 036-15 037;
45. d) S. Hofmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590-7593;
46. Angew. Chem. Int. Ed. 2005, 44, 7424-7426;
47. e) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299-4301;
48. Angew. Chem. Int. Ed. 2006, 45, 4193-4195;
49. f) S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 2006, 128, 13 074-13 075;
50. g) N.J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13 368-13 369;
51. h) J. W. Yang, B. List, Org. Lett. 2006, 8, 5653-5655.
52. a) S. G. Ouellet, J. B. Tuttle, D. W. C. MacMillan, L Am. Chem. Soc. 2005, 127, 32-33;
53. b) Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15 051-15 053;
54. c) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86;
55. d) J. B. Tuttle, S. G. Ouellet, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 12 662-12 663.
56. a) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781-3783;
57. b) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765-3768;
58. Angew. Chem. Int. Ed. 2006, 45, 3683-3686;
59. c) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 6903-6907;
60. Angew. Chem. Int. Ed. 2006, 45, 6751-6755.
61. G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2006, 47, 7417-7421.
62. a) H. Adolfsson, Angew. Chem. 2005, 117, 3404-3406;
63. Angew. Chem. Int. Ed. 2005, 44, 3340-3342;
64. b) J. Rosen, Chemtracts 2005, 18, 65-71.
65. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87.
66. For leading references, see: a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
67. Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
68. b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
69. Reviews on chiral Brønsted acid catalysis: a) S. J. Connon, Angew. Chem. 2006, 118, 4013-4016;
70. Angew. Chem. Int. Ed. 2006, 45, 3909-3912;
71. b) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010;
72. c) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573;
73. Angew. Chem. Int. Ed. 2006, 45, 1520-1543;
74. d) C. Bolm, T. Rantanen, I. Schiffers, L. Zani, Angew. Chem. 2005, 117, 1788-1793;
75. Angew. Chem. Int. Ed. 2005, 44, 1758-1763;
76. e) P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113;
77. Angew. Chem. Int. Ed. 2004, 43, 2062-2064;
78. f) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296.
79. S. Singh, U K. Batra, Indian J. Chem. Sect. B 1989, 25, 1-2.
80. a) S. Zehani, G. Gelbard, J. Chem. Soc. Chem. Commun. 1985, 1162-1163;
81. b) S. Zehani, J. Lin, G. Gelbard, Tetrahedron 1989, 45, 733-740.
82. For a study on polysiloxane-supported 1-benzyl-1,4-dihydronicotinamide, see: B. Zhang, X.-Q. Zhu, J.-Y. Lu, J. He, P. G. Wang, J.-P. Cheng, J. Org. Chem. 2003, 68, 3295-3298.