Chiral phosphoric acid catalyzed transfer hydrogenation: Facile synthetic access to highly optically active trifluoromethylated amines

Angewandte Chemie - International Edition

Volumn 50, Issue 35, 2011, Pages 8180-8183

  Henseler, Alexander ^a   Kato, Masanori ^a   Mori, Keiji ^a   Akiyama, Takahiko ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

asymmetric catalysis; fluorine; hydrogenation; organocatalysis; reductive amination

Indexed keywords

ASYMMETRIC CATALYSIS; FUNCTIONALIZED; KETIMINES; OPTICALLY ACTIVE; ORGANOCATALYSIS; REACTION CONDITIONS; REDUCTIVE AMINATION; SYNTHETIC UTILITY; TRANSFER HYDROGENATIONS;

CATALYSIS; FLUORINE; HYDROGENATION; KETONES; PHOSPHORIC ACID; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AMINES;

AMINE; FLUORINE; IMINE; KETIMINE; NITRILE; PHOSPHORIC ACID;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

AMINATION; AMINES; CATALYSIS; FLUORINE; HYDROGENATION; IMINES; NITRILES; OXIDATION-REDUCTION; PHOSPHORIC ACIDS; STEREOISOMERISM;

EID: 80051714758     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103240     Document Type: Article

References (69)

1. T. C. Nugent, M. El-Shazly, Adv. Synth. Catal. 2010, 352, 753-819
2. T. C. Nugent, in Chiral Amine Synthesis, Vol. 1 (Ed.:, T. C. Nugent,), Wiley-VCH, Weinheim, 2010, and references therein
3. N. Fleury-Brégot, V. de La Fuente, S. Castillon, C. Claver, ChemCatChem 2010, 2, 1346-1371
4. J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713-1760.
5. A. Volonterio, P. Bravo, M. Zanda, Org. Lett. 2000, 2, 1827-1830
6. A. Volonterio, P. Bravo, M. Zanda, Tetrahedron Lett. 2001, 42, 3141-3144
7. A. Volonterio, S. Bellosta, F. Bravin, M. C. Bellucci, L. Bruché, G. Colombo, L. Malpezzi, S. Mazzini, S. V. Meille, M. Meli, C. R. de Arellano, M. Zanda, Chem. Eur. J. 2003, 9, 4510-4522
8. M. Sani, A. Volonterio, M. Zanda, ChemMedChem 2007, 2, 1693-1700
9. H. J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637-643
10. P. Jeschke, ChemBioChem 2004, 5, 570-589
11. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330
12. W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369.
13. M. Molteni, A. Volonterio, M. Zanda, Org. Lett. 2003, 5, 3887-3890
14. M. Molteni, C. Pesenti, M. Sani, A. Volonterio, M. Zanda, J. Fluorine Chem. 2004, 125, 1735-1743.
15. S. Gomez, J. A. Peters, T. Maschmeyer, Adv. Synth. Catal. 2002, 344, 1037-1057
16. H.-U. Blaser, C. Malan, B. Pugin, F. Spinder, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103-151
17. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069. For asymmetric reductions of imines, see
18. C. Li, C. Wang, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2008, 130, 14450-14451
19. N. Mršić, A. J. Minnaard, B. L. Feringa, J. G. D. Vries, J. Am. Chem. Soc. 2009, 131, 8358-8359
20. G. Hou, F. Gosselin, W. Li, J. C. McWilliams, Y. Sun, M. Weisel, P. D. O'Shea, C.-Y. Chen, I. W. Davies, X. Zhang, J. Am. Chem. Soc. 2009, 131, 9882-9883
21. S. Zhou, S. Fleischer, K. Junge, S. Das, D. Addis, M. Beller, Angew. Chem. 2010, 122, 8298-8302
22. Angew. Chem. Int. Ed. 2010, 49, 8121-8125. For the asymmetric reductive aminations of ketones, see
23. R. P. Tripathi, S. S. Verma, J. Pandey, V. K. Tiwari, Curr. Org. Chem. 2008, 12, 1093-1115
24. L. Rubio-Pérez, F. J. Pérez-Flores, P. Sharma, L. Velasco, A. Cabrera, Org. Lett. 2008, 11, 265-268
25. C. Li, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2009, 131, 6967-6969
26. D. Steinhuebel, Y. Sun, K. Matsumura, N. Sayo, T. Saito, J. Am. Chem. Soc. 2009, 131, 11316-11317
27. C. Wang, A. Pettman, J. Basca, J. Xiao, Angew. Chem. 2010, 122, 7710-7714
28. Angew. Chem. Int. Ed. 2010, 49, 7548-7552.
29. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
30. M. Terada, Chem. Commun. 2008, 4097-4112
31. M. Terada, Synthesis 2010, 1929-1982. For pioneering work on chiral phosphoric acid catalysis, see
32. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594
33. Angew. Chem. Int. Ed. 2004, 43, 1566-1568
34. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
35. S. J. Connon, Org. Biomol. Chem. 2007, 5, 3407-3417
36. S.-L You, Chem. Asian J. 2007, 2, 820-827
37. M. Rueping, E. Sugiono, F. R. Schoepke, Synlett 2010, 852-865.
38. S. Hoffmann, A. Seayad, B. List, Angew. Chem. 2005, 117, 7590-7593
39. Angew. Chem. Int. Ed. 2005, 44, 7424-7427
40. M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781-3783
41. G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830-5831; For organocatalytic asymmetric reductive aminations of ketones, see
42. R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86
43. J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498-7499
44. M. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 5920-5922
45. Angew. Chem. Int. Ed. 2008, 47, 5836-5838
46. V. N. Wakchaure, J. A. Zhou, S. Hoffmann, B. List, Angew. Chem. 2010, 122, 4716-4718
47. Angew. Chem. Int. Ed. 2010, 49, 4612-4614. For theoretical studies, see
48. L. Simón, J. M. Goodman, J. Am. Chem. Soc. 2008, 130, 8741-8747
49. T. Marcelli, P. Hammar, F. Himo, Adv. Synth. Catal. 2009, 351, 525-529.
50. A. Suzuki, M. Mae, H. Amii, K. Uneyama, J. Org. Chem. 2004, 69, 5132-5134
51. H. Abe, H. Amii, K. Uneyama, Org. Lett. 2001, 3, 313-315; for enantioselective reductions of fluorinated α-iminophosphonates, see
52. N. S. Goulioukina, G. N. Bondarenko, S. E. Lyubimov, V. A. Davankov, K. N. Gavrilov, I. P. Beletskaya, Adv. Synth. Catal. 2008, 350, 482-492; for enantioselective reductions of perfluorinated N-acyl ketimines, see
53. K. Mikami, T. Murase, L. Zhai, S. Kawauchi, Y. Itoh, S. Ito, Tetrahedron Lett. 2010, 51, 1371-1373. For enantio- and diastereoselective trifluoromethylation of aldimines, see
54. W. Xu, R. William, J. Dolbier, J. Org. Chem. 2005, 70, 4741-4745
55. Y. Kawano, T. Mukaiyama, Chem. Lett. 2005, 34, 894-895
56. H. Kawai, A. Kusuda, S. Nakamura, M. Shiro, N. Shibata, Angew. Chem. 2009, 121, 6442-6445
57. Angew. Chem. Int. Ed. 2009, 48, 6324-6327
58. I. Fernandéz, V. Valdivia, A. Alcudia, A. Chelouan, N. Khiar, Eur. J. Org. Chem. 2010, 1502-1509; See also
59. L. Bernardi, E. Indrigo, S. Pollicino, A. Ricci, Chem. Commun. 2011, DOI:.
60. G. Hughes, P. N. Devine, J. R. Naber, P. D. O'Shea, B. S. Foster, D. J. McKay, R. P. Volante, Angew. Chem. 2007, 119, 1871-1874
61. Angew. Chem. Int. Ed. 2007, 46, 1839-1842
62. J. Xua, Z.-J. Liub, X.-J. Yang, L.-M. Wang, G.-L. Chen, J.-T. Liub, Tetrahedron 2010, 66, 8933-8937.
63. N. Allendörfer, A. Sudau, S. Bräse, Adv. Synth. Catal. 2010, 352, 2815-2824.
64. M.-W. Chen, Y. Duan, Q.-A. Chen, D.-S. Wang, C.-B. Yu, Y.-G. Zhou, Org. Lett. 2010, 12, 5075-5077.
65. C. Zhu, T. Akiyama, Adv. Synth. Catal. 2010, 352, 1846-1850
66. C. Zhu, T. Akiyama, Org. Lett. 2009, 11, 4180-4183.
67. For an additional example where a benzothiazoline derivative was used as transfer hydrogenation agent in preference to Hantzsch ester, see:, D. Enders, J. X. Liebich, G. Raabe, Chem. Eur. J. 2010, 16, 9763-9766.
68. S. F. Poon, D. J. St. Jean, P. E. Harrington, C. Henley, J. Davis, S. Morony, F. D. Lott, J. D. Reagan, J. Y. L. Lu, Y. H. Yang, C. Fotsch, J. Med. Chem. 2009, 52, 6535-6538.
69. J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, P. L. Alsters, F. L. van Delft, F. P. J. T. Rutjes, Tetrahedron Lett. 2006, 47, 8109-8113.