Phenolic N-oxide as a highly efficient organocatalyst for cyanosilylation of ketones

Synlett

Volumn , Issue 9, 2004, Pages 1598-1600

  Li, Yan ^a   He, Bin ^a   Feng, Xiaoming ^a,b   Zhang, Guolin ^c  

^a SICHUAN UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

^c CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

Achiral N oxides; Catalysis; Cyanohydrins; Ketones; Organocatalysis

Indexed keywords

KETONE; OXIDE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; SILYLATION;

EID: 3943088326     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829072     Document Type: Article

References (53)

1. (a) Gregory, R. J. H. Chem. Rev. 1999, 99, 3649.
2. (b) North, M. Tetrahedron: Asymmetry 2003, 14, 147.
3. 3: Matsubara, S.; Takai, T.; Utimoto, K. Chem. Lett. 1991, 1447.
4. 3: Yang, Y.; Wang, D. Synlett 1997, 861.
5. 2: Saravanan, P.; Anand, R. V.; Singh, V. K. Tetrahedron Lett. 1998, 39, 3823.
6. 2: Gassman, P. G.; Talley, J. J. Tetrahedron Lett. 1978, 19, 3773.
7. 3: Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Tetrahedron Lett. 2001, 42, 3041.
8. (f) LiOR: Wilkinson, H. S.; Grover, P. T.; Vandenbossche, C. P.; Bakale, R. P.; Bhongle, N. N.; Wald, S. A.; Senanayake, C. H. Org. Lett. 2001, 3, 553.
9. 4: Jenner, G. Tetrahedron Lett. 1999, 40, 491.
10. 2: Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 2525.
11. 2: Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.; Rossi, M. Synlett 1999, 315.
12. 2: Ward, D. E.; Hrapchak, M. J.; Sales, M. Org. Lett. 2000, 2, 57.
13. 3/chiral peptide ligand: Deng, H.-B.; Isler, M. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2002, 41, 1009.
14. Greenlee, W. J.; Hangauer, D. G. Tetrahedron Lett. 1983, 24, 4559.
15. Higuchi, K.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1993, 66, 2016.
16. (a) Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412.
17. (b) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691.
18. (c) Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
19. (d) Yabu, K.; Masumoto, S.; Kanai, M.; Curran, D. P.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2923.
20. (e) Masumoto, S.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 8647.
21. (a) Shen, Y.-C.; Feng, X.-M.; Li, Y.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2002, 793.
22. (b) Shen, Y.-C.; Feng, X.-M.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2002, 1353.
23. (c) Shen, Y.-C.; Feng, X.-M.; Li, Y.; Zhang, G.-L.; Jiang, Y.-Z. Tetrahedron 2003, 59, 5667.
24. (d) Shen, Y.-C.; Feng, X.-M.; Li, Y.; Zhang, G.-L.; Jiang, Y.-Z. Eur. J. Org. Chem. 2004, 129.
25. (a) Chen, F.-X.; Feng, X.-M.; Qin, B.; Zhang, G.-L.; Jiang, Y.-Z. Org. Lett. 2003, 5, 949.
26. (b) Chen, F.-X.; Feng, X.-M.; Qin, B.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2003, 558.
27. (a) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726.
28. (b) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem. Int. Ed. 2003, 42, 2785.
29. (c) Juhl, K.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 1498.
30. (d) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem. Int. Ed. 2003, 42, 3677.
31. (e) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661.
32. (f) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16.
33. (g) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475.
34. (h) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151.
35. (i) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F. III Org. Lett. 2003, 5, 1685.
36. (j) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249.
37. (k) Cordova, A.; Barbas, C. F. III Tetrahedron Lett. 2003, 44, 1923.
38. (l) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159.
39. (m) Zhong, G. Angew. Chem. Int. Ed. 2003, 42, 4247.
40. (n) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. III Angew. Chem. Int. Ed. 2003, 42, 4233.
41. (o) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
42. (a) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195.
43. (b) Tian, S.-K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
44. (a) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. I. J. Am. Chem. Soc. 1998, 120, 6419.
45. (b) Shimada, T.; Kina, A.; Hayashi, T. J. Org. Chem. 2003, 68, 6329.
46. (c) Malkov, A. V.; Bell, M.; Orsini, M.; Pernazza, D.; Massa, A.; Herrmann, P.; Meghani, P.; Kočovský, P. J. Org. Chem. 2003, 68, 9659.
47. Derdau, V.; Laschat, S.; Hupe, E.; Konig, W. A.; Dix, I.; Jones, P. G. Eur. J. Inorg. Chem. 1999, 1001.
48. O'Neil, I. A.; Turner, C. D.; Kalindjian, S. B. Synlett 1997, 777.
49. Tao, B.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 353.
50. Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
51. (a) Liu, B.; Feng, X.-M.; Chen, F.-X.; Zhang, G.-L.; Jiang, Y.-Z. Synlett 2001, 1551.
52. (b) Jiao, Z.-G.; Feng, X.-M.; Liu, B.; Chen, F.-X.; Zhang, G.-L.; Jiang, Y.-Z. Eur. J. Org. Chem. 2003, 3818.
53. 2O-petroleum ether (1:100, v/v) to give the pure product.