A remarkable titanium-catalyzed asymmetric strecker reaction using hydrogen cyanide at room temperature

Advanced Synthesis and Catalysis

Volumn 352, Issue 13, 2010, Pages 2153-2158

  Ramalingam, Balamurugan ^a   Seayad, Abdul Majeed ^a   Chuanzhao, Li ^a   Garland, Marc ^a   Yoshinaga, Kazuhiko ^b   Wadamoto, Manabu ^b   Nagata, Takushi ^b   Chai, Christina L L ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^b Mitsui Chemicals Asia Pacific Ltd   (Singapore)

Author keywords

Enantioselective cyanation; Hydrogen cyanide; Imines; In situ ir studies; Strecker reaction; Titanium catalyst

Indexed keywords

EID: 77956908389     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000462     Document Type: Article

References (76)

1. a) C. Nájera, J. M. Sansano, Chem. Rev. 2007, 707, 4584-4671;
2. b) K. Harada, Nature 1963, 200, 1201.
3. A. Strecker, Ann. Chem. Pharm. 1850, 75, 27-45.
4. M. S. Iyer, K. M. Gigstad, N. D. Namdev, M. Lipton, J. Am. Chem. Soc. 1996, 118, 4910-4911.
5. Reviews on enantioselective Strecker reaction:
6. a) P. Merino, E. Marqués-López, T. Tejero, R. P. Herrera, Tetrahedron 2009, 65, 1219-1234;
7. b) C. Spino, Angew. Chem. 2004, 116, 1796-1798;
8. Angew. Chem. Int. Ed. 2004, 43, 1764-1766;
9. H. Gröger, Chem. Rev. 2003, 103, 2795-2827;
10. L. Yet, Angew. Chem. 2001, 113, 900-902;
11. Angew. Chem. Int. Ed. 2001, 40, 875-877;
12. e) A. Mori, S. Inoue, in: Comprehensive Asymmetric Catalysis, Vol. 2, (Eds. : E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Spiringer, Berlin, 1999, pp 983-994.
13. Cyanation of aldimines using HCN by organocatalysts: a)E.J. Corey, M.J. Grogan, Org. Lett. 1999, 1, 157160;
14. b) M. S. Sigman, P. Vachal, E. N. Jacobsen, Angew. Chem. 2000, 112, 1336-1338;
15. Angew. Chem. Int. Ed. 2000, 39, 1279-1281;
16. P. Vachal, E.N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012-10014;
17. J. Huang, E. J. Corey, Org. Lett. 2004, 6, 5027-5029;
18. e) M. Ruep-ing, E. Sugiono, C. Azap, Angew. Chem. 2006, 118, 2679-2681;
19. Angew. Chem. Int. Ed. 2006, 45, 2617-2619.
20. For acylcyanation of imines: a) S. C. Pan, J. Zhou, B. List, Synlett 2006, 3275-3276;
21. b) S. C. Pan, J. Zhou, B. List, Angew. Chem. 2007, 119, 618-620;
22. Angew. Chem. Int. Ed. 2007, 46, 612-614;
23. S. C. Pan, B. List, Chem. Asian J. 2008, 3, 430-437. For cyanation using KCN, see:
24. T. Ooi, Y Uematsu, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 2548-2549;
25. e) R. Reingruber, T. Baumann, S. Dahmen, S. Bräse, Adv. Synth. Catal. 2009, 357, 1019-1024;
26. f) S. J. Zuend, M. P. Coughlin, M. P. Lalonde, E. N. Jacobsen, Nature 2009, 461, 968-971.
27. Cyanation of keto imines by organocatalysts:
28. a) P. Vachal, E. N. Jacobsen, Org. Lett. 2000, 2, 867-870;
29. b) Rueping, E. Sugiono, S. A. Moreth, Adv. Synth. Catal. 2007, 349, 759-764;
30. J. Huan , X. Liu, Y. Wen, B. Qin, X. Feng, J. Org. Chem. 2007, 72, 204-208;
31. J. Wang, X. Hu, J. Jiang, S. Gou, X. Huang, X. Liu, X. Feng, Angew. Chem. 2007, 119, 8620-8622;
32. Angew. Chem. Int. Ed. 2007, 46, 8468-8470;
33. e) Z. Hou, J. Wang, X. Liu, X. Feng, Chem. Eur. J. 2008, 14, 44844486;
34. f) K. Shen, X. Liu, Y Cai, L. Lin, X. Feng, Chem. Eur. 7.2009, 25, 6008-6014.
35. Cyanation of aldimines using HCN by metal catalysts: a) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 720, 5315-5316;
36. b) S. Kobayashi, H. Ishitani, Chirality, 2000, 12, 540-543.
37. Cyanation of aldimines using TMSCN: a) C. A. Krueger, K. W. Kuntz, C. W. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999,121, 4284-4285;
38. b) M. Takamura, Y. Hamashima, H. Usuda, M. Kanai, M. Shibasaki, Angew. Chem. 2000, 112, 1716-1718;
39. Angew. Chem. Int. Ed. 2000, 39, 1650-1652;
40. M. Takamura, Y. Hamashima, H. Usuda, M. Kanai, M. Shibasaki, Chem. Pharm. Bull. 2000, 48, 1586-1592;
41. J.J. Byrne, M. Chavarot, P.Y. Chavant, Y Valleé, Tetrahedron Lett. 2000, 41, 873- 876;
42. e) N. S. Josephson, K.W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 1159411599;
43. f) W. Mansawat, W. Bhanthumnavin, T. Vilaivan, Tetrahedron Lett. 2003, 44, 3805-3808;
44. g) V. Banphavichit, W. Mansawat, W. Bhanthumnavin, T. Vilaivan, Tetrahedron 2004, 60,10559-10568;
45. h) V. Banphavichit, W. Bhanthumnavin, T. Vilaivan, Tetrahedron 2007, 63, 8727-8734;
46. M. Hatano, Y. Hattori, Y. Furuya, K. Ishihara, Org. Lett. 2009, 11, 2321-2324;
47. 3SnCN as cyanide source:
48. k)H. Ishitani, S. Komiyama, S. Kobayashi, Angew. Chem. 1998, 110, 3369-3372;
49. Angew. Chem. Int. Ed. 1998, 37, 3186-3188;
50. H. Ishitani, S. Komiyama, Y. Hasegawa, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 762-766.
51. Cyanation of ketoimines by metal catalysts:
52. a) J. J. Byrne, M, Chavarot, P. Y. Chavant, Y. Valleé, Tetrahedron Lett. 2000, 41, 873-876;
53. b) S. Masumoto, H. Usuda, M. Suzuki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 5634-5635;
54. N. Kato, M. Suzuki, M. Kanai, M. Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153-3155;
55. J.P. Abell, H. Yamamoto, J. Am. Chem. Soc. 2009, 131, 15118-15119.
56. [6f];
57. [6f];
58. [9a];
59. for cyanation at 23°C using TMSCN, see: A.M. Seayad, B. Ramalingam, K. Yoshinaga, T. Nagata, C. L. L. Chai, Org. Lett. 2010 ,12, 264-267;
60. e) A. M. Seayad, C. L. L. Chai, B. Ramalingam, T. Nagata, K. Yoshinaga, PCT Int. Appl. WO2008121074, 2008.
61. [3]
62. Partially hydrolyzed titanium alkoxide (PHTA) was prepared by hydrolysing Ti(O-H-Bu)4́ using controlled amount of water or inorganic hydrate, see;
63. a) K. Yoshinaga, T. Nagata, Adv. Synth. Catal. 2009, 351, 14951498;
64. [11d]
65. HCN is an extremely poisonous liquid and boils at 26 °C. Proper safety precautions will need to be adhered to and appropriate safety equipment for example, cyanide detector and personal protection equipment MUST be used. Reactions must be carried out in a well ventilated fume hood.
66. A toluene solution of 0.50M HCN was used for the cyanation reactions. HCN was prepared from KCN as reported: K. Ziegler, Org. Synth. Coll. Vol. 1941, 1, 314316. The concentration of HCN was determined by photometric titration using the 'cyanide tesť kit available in Merck.
67. See Supporting Information for further details.
68. V. Banphavichit, W. Mansawat, W. Bhanthumnavin, T. Vilaivan, Tetrahedron 2009, 65, 5849-5854.
69. N. Kolla, C. R. Elati, M. Arunagiri, S. Gangula, P. J. Vankawala, Y. Anjaneyulu, A. Bhattacharya, S. Venkatrama, V. T. Mathad, Org. Process Res. Dev. 2007, 11, 455-457.
70. H. Nanba, Y. Yasohara, J. Hasegawa, S. Takahashi, Org. Process Res. Dev. 2007, 11, 503-508.
71. a) Y. N. Belokon', B. Green, N. S. Ikonnikov, V. S. Larichev, B. V. Lokshin, M. A. Moscalenko, M. North, C. Orizu, A. S. Peregudov, G. I. Timofeeva, Eur J. Org. Chem. 2000, 2655-2661;
72. b) K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th edn., Wiley, New York, 1986, pp 272-280;
73. -1 were assigned to bridging Ti-O-Ti vibrations by DFT calculations, see: I. S. Ignatyev, M. Montejo, J.J. López González, J. Phys. Chem. A: 2007, 111, 7973-7979.
74. 8) obtained for the catalyst suggests the possible formation of oligomeric species. Metal alkoxides are prone to hydrolysis and form oligomeric metal oxo-alkoxide complexes, see:
75. a) D. C. Bradley, I. P. Mehrotra, I. P. Rothwell, A. Singh, Alkoxo and Aryloxo Derivatives of Metals, Academic Press, London, 2001, pp. 405-411;
76. b) R. Papiernik, L. G. Hubert-Pfalzgraf, J. Vaissermann, M. C. H. B. Gonclaves, J. Chem. Soc. Dalton Trans. 1998, 22852287.