Vanadium(V) salen complex catalyzed highly enantioselective cyanoformylation of aldehydes in the presence of imidazole as a cocatalyst

European Journal of Organic Chemistry

Volumn , Issue 26, 2008, Pages 4511-4515

  Khan, Noor Ul H ^a   Agrawal, Santosh ^a   Kureshy, Rukhsana I ^a   Abdi, Sayed H R ^a   Jeya Prathap, K ^a   Jasra, Raksh V ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Aldehydes; Asymmetric catalysis; Cyanides; Nitrogen heterocycles; Vanadium

Indexed keywords

EID: 53849083821     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800476     Document Type: Article

References (64)

1. For reviews on the synthesis and applications of cyanohydrins, see: a) M. North in Science of Synthesis (Ed.: S.-I. Murahashi), Thieme, Stuttgart, 2004, vol. 19, pp. 235-284;
2. b) M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989-1999;
3. c) M. B. Smith, J. March, March's Advanced Organic Chemistry, 5th ed., John Wiley & Sons, New York, 2001, pp. 1239-1240;
4. d) I. Ojima, Catalytic Asymmetric Synthesis, Wiley, New York, 2000, pp. 235-284;
5. e) A. Mori, S. Inoue, "Cyanation of Car bonyl and Amino Groups" in Comprehensive Asymmetric Synthesis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, pp. 983-992;
6. f) F. Effenberger, Angew. Chem. 1994, 106, 1609-1619;
7. Angew. Chem. Int. Ed. Engl. 1994, 33, 1555-1564.
8. a) T. Kusumoto, T. Hanamoto, T. Hiyama, S. Takehera, T. Shoji, M. Osawa, T. Kuriyama, K. Nakamura, T. Fujisawa, Chem. Lett. 1990, 19, 1615-1618;
9. b) R. J. A. Thierry, A. C. Lisa, N. Michael, Synlett 2005, 125, 1828-1847;
10. c) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 125, 1491-1508;
11. d) F.-X. Chen, X.-M. Feng, Synlett 2005, 125, 892-899;
12. e) J. M. Brunel, I. P. Holmes, Angew. Chem. Int. Ed. 2004, 43, 2752-2778;
13. f) N. Michael, Tetrahedron: Asymmetry 2003, 14, 147-176;
14. g) R. J. H. Gregory, Chem. Rev. 1999, 99, 3649-3682.
15. a) Y. N. Belokon, A. V. Gutnov, M. A. Moskalenko, L. V. Yashkina, D. E. Lesovoy, N. S. Ikonnikov, V. S. Larichev, M. North, Chem. Commun. 2002, 244-245;
16. b) Y. N. Belokon, S. C. Cepas, B. Green, N. S. Ikonnikov, V. N. Khrustalev, V. S. Larichev, M. A. Moscalenko, M. North, C. Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva, L. V. Yashkina, J. Am. Chem. Soc. 1999, 121, 3968-3973;
17. c) Y. N. Belokon, V. I. Maleev, M. North, D. L. Usanov, Chem. Commun. 2006, 4614-4616;
18. d) W. Huang, Y. Song, J. Wang, G. Cao, Z. Zheng, Tetrahedron 2004, 60, 10469-10477;
19. e) Y. N. Belokon, M. North, V. I. Maleev, N. V. Voskoboev, M. A. Moskalenko, A. S. Peregudov, A. V. Dmitriev, N. S. Ikonnikov, H. B. Kagan, Angew. Chem. Int. Ed. 2004, 43, 4085-4089;
20. f) Y. N. Belokon, P. Carta, A. V. Gutnov, V. Maleeev, M. A. Moskalenko, L. V. Yashkina, N. S. Ikonnikov, N. V. Voskoboev, V. N. Khrustalev, M. North, Helevetica. Chim. Acta 2002, 85, 3301-3312;
21. g) Y. N. Belokon, M. North, T. Parsons, Org. Lett. 2000, 2, 1617-1619;
22. h) Y. N. Belokon, B. Green, N. S. Ikonnikov, M. North, T. Parsons, V. I. Taravov, Tetrahedron 2001, 57, 771-779.
23. a) Y. Xiong, X. Huang, S.-H. Gou, J.-L. Huang, Y.-H. Wen, X.-M. Feng, Adv. Synth. Catal. 2006, 348, 538-544;
24. b) X.-H. Liu, B. Qin, X. Zhou, B. He, X.-M. Feng, J. Am. Chem. Soc. 2005, 127, 12224-12225;
25. c) H.-D. Ryu, E. J. Corey, J. Am. Chem. Soc. 2005, 127, 5384-5387;
26. d) D. E. Fuerst, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 8964-8965;
27. e) Y.-H. Wen, X. Huang, J.-L. Hang, Y. Xiong, B. Qin, X.-M. Feng, Synlett 2005, 125, 2445-2447;
28. f) Y. C. Qin, L. Liu, L. Pu, Org. Lett. 2005, 7, 2381-2383;
29. g) Y. Li, B. He, B. Qin, X.-M. Feng, G.-L. Zhang, J. Org. Chem. 2004, 69, 7910-7913;
30. h) S.-K. Tian, R. Hong, L. Deng, J. Am. Chem. Soc. 2003, 125, 9901-9901;
31. i) H. Griengl, A. Hickel, D. V. Johnson, C. Kratky, M. Schmidt, H. Schwab, Chem. Commun. 1997, 1933-1940;
32. j) F. Effenberger, Chimia 1999, 53, 3-10;
33. k) M. Schmidt, H. Griengl, Top. Curr. Chem. 1999, 200, 193-226;
34. l) G. Seoane, Curr. Org. Chem. 2000, 4, 283-304.
35. a) N. Yamagiwa, J. Tian, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 3413-3422;
36. b) J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Org. Lett. 2003, 5, 3021-3024;
37. c) J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. Int. Ed. 2002, 41, 3636-3638.
38. a) Y. N. Belokon, A. J. Blacker, L. A. Clutterbuck, N. Michael, Tetrahedron 2004, 60, 10433-10447;
39. b) Y. N. Belokon, A. J. Blacker, L. A. Clutterbuck, M. North, Org. Lett. 2003, 5, 4505-4508;
40. c) Y. N. Belokon, E. Ishibashi, H. Nomura, M. North, Chem. Commun. 2006, 1775-1777;
41. d) Y. N. Belokon, W. Clegg, R. W. Harrington, C. Young, M. North, Tetrahedron 2007, 63, 5287-5299;
42. e) Y. N. Belokon, W. Clegg, R. W. Harrington, E. Ishibashi, H. Nomura, M. North, Tetrahedron 2007, 63, 9724-9740.
43. a) S.-K. Tian, L. Deng, J. Am. Chem. Soc. 2001, 123, 6195-6196;
44. b) H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948-8949;
45. c) S.-K. Tian, L. Deng, Tetrahedron 2006, 62, 11320-11330;
46. d) S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. MaDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621-631.
47. a) S. Lundgren, E. Wingstrand, M. Penhoat, C. Moberg, J. Am. Chem. Soc. 2005, 127, 11592-11593;
48. b) S. Lundgren, E. Wingstrand, C. Moberg, Adv. Synth. Catal. 2007, 349, 364-372.
49. a) A. Baeza, J. Casas, C. Nájera, J. Sansano, J. M. Saá, Eur. J. Org. Chem. 2006, 1949-1958;
50. b) A. Baeza, C. Nájera, J. Sansano, J. M. Saá, Tetrahedron: Asymmetry 2005, 16, 2385-2389;
51. c) J. Casas, A. Baeza, J. M. Sansano, C. Nájera, J. M. Saá, Tetrahedron: Asymmetry 2003, 14, 197-200;
52. d) A. Baeza, J. Casas, C. Nájera, J. Sansano, J. M. Saá, Angew. Chem. Int. Ed. 2003, 42, 3143-3146.
53. a) Q. Li, L. Chang, X. Liu, X. Feng, Synlett 2006, 1675-1678;
54. b) S. Gou, X. H. Chen, Y. Xiong, X. Feng, J. Org. Chem. 2006, 71, 5732-5736;
55. c) S. K. Chen, D. Peng, H. Zhou, L. W. Wang, F. X. Chen, X. Feng, Eur. J. Org. Chem. 2007, 639-644;
56. d) S. Gou, J. Wang, X. Liu, W. Wang, F. X. Chen, X. Feng, Adv. Synth. Catal. 2007, 349, 343-349.
57. a) N. H. Khan, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, V. J. Mayani, R. V. Jasra, Tetrahedron: Asymmetry 2006, 17, 2659-2666;
58. b) N. H. Khan, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, V. J. Mayani, R. V. Jasra, J. Mol. Catal. A: Chem. 2007, 264, 140-145;
59. c) N. H. Khan, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, V. J. Mayani, R. V. Jasra, Eur. J. Org. Chem. 2006, 3175-3180;
60. d) N. H. Khan, R. I. Kureshy, S. H. R. Abdi, S. Agrawal, R. V. Jasra, Coord. Chem. Rev. 2008, 252, 593-623;
61. e) N. H. Khan, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, K. J. Prathap, R. V. Jasra, Chirality 2008 (DOI: 10.1002/chir. 20534; in press).
62. V. A. Soloshonk, Angew. Chem. Int. Ed. 2006, 45, 766-769.
63. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, Pergamon, New York, 1981.
64. J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939-1942.