N-methylmorpholine N-oxide: A rare nonmetallic catalyst for the most efficient silylcyanation of aldehydes

Synthetic Communications

Volumn 34, Issue 16, 2004, Pages 2973-2980

  Kim, Sung Soo ^a   Rajagopal, Gurusamy ^a,b   Kim, Dong Won ^a   Song, Dae Ho ^a  

^a Inha University   (South Korea)

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

Author keywords

Aldehydes; NMO; Silylcyanation; TMSCN

Indexed keywords

4 METHYLMORPHOLINE N OXIDE; ALDEHYDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; METAL; MORPHOLINE DERIVATIVE; TRIMETHYLSILYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYANATION; METHODOLOGY; SILYLCYANATION;

EID: 4544263813     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200026652     Document Type: Article

References (20)

1. (a) Gregory, R.J.H. Chem. Rev. 1999, 99, 3649;
2. (b) Evans, D.A.; Truesdake, L.K.; Carroll, G.L. J. Chem. Soc. 1973, 2, 55;
3. (c) Lidy, W.; Sundermeyer, W. Tetrahedron Lett. 1973, 9, 1449;
4. (d) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 4, 537.
5. Whitesell, J.K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 2525.
6. Saravanan, P.; Vijaya, R.; Singh, V.K. Tetrahedron Lett. 1998, 39, 3823.
7. Jenner, G. Tetrahedron Lett. 1999, 40, 491.
8. Curini, M.; Epifan, F.; Marcotullio, M.C.; Rosati, O.; Rossi, M. Synlett 1999, 315.
9. (a) Bandini, M.; Cozzi, P.G.; Melchiorre, P.; Umani-Roncohi, A. Tetrahedron Lett. 2001, 42, 3041;
10. (b) Bandini, M.; Cozzi, P.G.; Garelli, A.; Melchiorre, P.; Umani-Ronchi, A. Eur. J. Org. Chem. 2002, 3243.
11. (a) Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Synlett 2003, 793;
12. (b) Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Synlett 2003, 558;
13. (c) Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Tetrahedron 2003, 59, 5667.
14. (a) Pan, W.; Feng, X.; Gong, L.; Hu, W.; Li, Z.; Mi, A.; Jiang, Y. Synlett 1996, 337;
15. (b) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327.
16. Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641.
17. Belokon, Y.N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N.S.; Khrustalev, V.N.; Larichev, V.S.; Moscalenko, M.A.; North, M.; Orizu, C.; Tararov, V.I.; Tasinazzo, M.; Timofeeva, G.I.; Yashikina, L.V. J. Am. Chem. Soc. 1999, 121, 3968.
18. Belokon, Y.N.; North, M.; Parsons, T. Org. Lett. 2000, 2, 1617.
19. Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.I. J. Am. Chem. Soc. 1998, 120, 6419-6420.
20. Derdau, V.; Laschat, S.; Hupe, E.; Konig, W.A.; Dix, I.; Jones, P.G. Eur. J. Inorg. Chem. 1999, 1001-1007.