Strecker reaction of aldimines catalyzed by a nucleophilic N-heterocyclic carbene

Synthesis

Volumn , Issue 12, 2006, Pages 1937-1939

  Fukuda, Yoshimasa ^a   Maeda, Yuka ^a   Kondo, Kazuhiro ^a   Aoyama, Toyohiko ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Aldimine; Cyanation; Imidazolium salt; N heterocyclic carbene; Strecker reaction

Indexed keywords

CATALYSIS; CATALYSTS; REACTION KINETICS; SALTS;

ALDIMINE; IMIDAZOLIUM SALT; N-HETEROCYCLIC CARBENE; STRECKER REACTION;

AMINES;

(CYANOCPHENYLMETHYL)CARBAMIC ACID TERT BUTYL ESTER; 1,3 BIS(2,4,6 TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE; ALDIMINE DERIVATIVE; CARBENE; CYANIDE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; IMINE; N (1 CYANO 2 PHENYLPROPYL) 4 METHYLBENZENESULFONAMIDE; N (1 CYANO 3,3 DIMETHYLBUTYL) 4 METHYLBENZENESULFONAMIDE; N (CYANOCPHENYLMETHYL) 2,4,6 TRIISOPROPYLBENZENESULFONAMIDE; N (CYANOCYCLOHEXYLMETHYL) 4 METHYLBENZENESULFONAMIDE; N (CYANOPHENYLMETHYL) 4 METHYLBENZENESULFONAMIDE; N [4 (CHLOROPHENYL)CYANOMETHYL] 4 METHYLBENZENESULFONAMIDE; SULFONAMIDE; TRIMETHYLSILYL CYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYANATION; STRECKER SYNTHESIS;

EID: 33745741904     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942376     Document Type: Article

References (25)

1. For reviews, see: (a) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
2. (b) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1291.
3. For reviews, see: (a) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem. Int. Ed. 2004, 43, 5130.
4. (b) Grasa, G. A.; Singh, R.; Nolan, S. P. Synthesis 2004, 971.
5. For examples, see: (c) Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914.
6. (d) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
7. (e) Suzuki, Y.; Toyota, T.; Imada, F.; Sato, M.; Miyashita, A. Chem. Commun. 2003, 1314.
8. (f) Singh, R.; Kissling, R. M.; Letellier, M.-A.; Nolan, S. P. J. Org. Chem. 2004, 69, 209.
9. (g) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
10. (h) Burstein, C.; Glorius, F. Angew. Chem. Int. Ed. 2004, 43, 6205.
11. (i) Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347.
12. (j) Ye, W.; Cai, G.; Zhuang, Z.; Jia, X.; Zhai, H. Org. Lett. 2005, 7, 3769.
13. Cyanosilylation of aldehyde: (a) Fukuda, Y.; Maeda, Y.; Ishii, S.; Kondo, K.; Aoyama, T. Synthesis 2006, 589.
14. Cyanophosphorylation of aldehyde: (b) Fukuda, Y.; Maeda, Y.; Kondo, K.; Aoyama, T. Chem. Pharm. Bull. 2006, 54, 397.
15. For reviews, see: (a) Gröger, H. Chem. Rev. 2003, 103, 2795.
16. (b) Yet, L. Angew. Chem. Int. Ed. 2001, 40, 875.
17. 3OD at r.t.: He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131.
18. Selected recent examples: (a) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2000, 39, 1650.
19. (b) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2000, 48, 1586.
20. (c) Huang, J.; Corey, E. J. Org. Lett. 2005, 6, 5027.
21. (d) Banphavichit, V.; Mansawat, W.; Bhanthumnavin, W.; Vilaivan, T. Tetrahedron 2004, 60, 10559.
22. (e) Nakamura, S.; Sato, N.; Sugimoto, M.; Toru, T. Tetrahedron: Asymmetry 2004, 15, 1513.
23. (f) Jiao, Z.; Feng, X.; Liu, B.; Chen, F.; Zhang, G.; Jiang, Y. Eur. J. Org. Chem. 2003, 3818.
24. (g) Mansawat, W.; Bhanthumnavin, W.; Vilaivan, T. Tetrahedron Lett. 2003, 44, 3805.
25. Jennings, W. B.; Lovely, C. J. Tetrahedron Lett. 1988, 29, 3725.