Mild and Efficient Silylcyanation of Ketones Catalyzed by N-Methylmorpholine N- Oxide

Synthesis

Volumn , Issue 2, 2004, Pages 213-216

  Kim, Sung Soo ^a   Kim, Dong Won ^a   Rajagopal, Gurusamy ^a,b  

^a Inha University   (South Korea)

^b B S ABDUR RAHMAN CRESCENT INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

Cyanohydrins; Ketone; NMO; Silylcyanation; TMSCN

Indexed keywords

ADDITION REACTIONS; CATALYSIS; ETHERS;

CHIRALITY; SILYLCYANATION;

KETONES;

4 METHYLMORPHOLINE N OXIDE; KETONE; MORPHOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CYANATION; REACTION ANALYSIS; SILYLATION;

EID: 1242341211     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44380     Document Type: Article

References (32)

1. Griengel, H.; Hickel, A.; Johnson, D. V.; Kratky, C.; Schmidt, M.; Schwab, H. Chem. Commun. 1997, 1933; and references cited therein.
2. (a) Gregory, R. J. H. Chem. Rev. 1999, 99, 3649.
3. (b) Shan, G. M.; Hammer, R. P.; Ottea, J. A. J. Agric. Food Chem. 1997, 45, 4466.
4. (c) Galin, F. Z.; Rakhimov, R. H.; Tolstikov, G. A. Russ. Chem. Bull. 1998, 47, 530.
5. (a) North, M. Synlett 1993, 807.
6. (b) Deng, H.; Ister, M. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2002, 41, 1009.
7. (c) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181.
8. (d) Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515.
9. (e) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537.
10. (f) Hanashima, Y.; Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2001, 57, 805.
11. (g) Tian, S. K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
12. (a) Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Abdul Malik, K. M.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387.
13. (b) Belokon, Y.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 40, 8147.
14. (c) Belokon, Y.; Green, B.; Ikonnikov, N. S.; North, M.; Parsons, T.; Tararov, V. I. Tetrahedron 2001, 57, 771.
15. (a) Hanashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412.
16. (b) Hanashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691.
17. (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.
18. Bolm, C.; Muller, P. Tetrahedron Lett. 1995, 36, 1625.
19. Rowlands, G. J. Synlett 2003, 236.
20. Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Org. Lett. 2003, 5, 949.
21. Belokon, Y.; North, M.; Parsons, T. Org. Lett. 2000, 2, 1617.
22. Aspinall, H. C.; Greeves, N.; Smith, P. M. Tetrahedron Lett. 1999, 40, 1763.
23. Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Ronchi, A. V. Tetrahedron Lett. 2001, 42, 3041.
24. (a) Whitesell, J. K.; Podaca, R. A. Tetrahedron Lett. 1996, 37, 2525.
25. (b) Saravanan, P.; Vijaya Anand, R.; Singh, V. K. Tetrahedron Lett. 1998, 39, 3823.
26. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.; Rossi, M. Synlett 2002, 315.
27. Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Synlett 2003, 558.
28. (a) Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Tetrahedron 2003, 59, 5667.
29. (b) Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Synlett 2002, 793.
30. Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. I. J. Am. Chem. Soc. 1998, 120, 6419.
31. Derdau, V.; Laschat, S.; Hupe, E.; Konig, W. A.; Dix, I.; Jones, P. G. Eur. J. Inorg. Chem. 1999, 1001.
32. O'Neil, I. A.; Turner, C. D.; Kalindjian, S. B. Synlett 1997, 777.