Catalytic acylcyanation of imines with acetylcyanide

Synlett

Volumn , Issue 19, 2006, Pages 3275-3276

  Pan, Subhas Chandra ^a   Zhou, Jian ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

amino nitrile; Acetyl cyanide; Acylcyanation; Br nsted acid catalysis; Organocatalysis

Indexed keywords

ACETYLCYANIDE; ALIPHATIC COMPOUND; CYANIDE; IMINE; NITRILE; THIOUREA DERIVATIVE;

ACYLCYANATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY;

EID: 33845634715     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951543     Document Type: Article

References (29)

1. For reviews, see: (a) Gröger, H. Chem. Rev. 2003, 103, 2795.
2. (b) Yet, L. Angew. Chem. Int. Ed. 2001, 40, 875.
3. (c) Spino, C. Angew. Chem. Int. Ed. 2004, 43, 1764.
4. (a) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem. Int. Ed. 2002, 41, 3636.
5. (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2003, 5, 3021.
6. (c) Yamagiwa, N.; Tian, J.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 3413.
7. (d) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6295.
8. (e) Casas, J.; Baeza, A.; Sansano, J. M.; Nájera, C.; Saá, J. M. Tetrahedron: Asymmetry 2003, 14, 197.
9. (f) Belokon, Y. N.; Blacker, A. J.; Clutterbuck, L. A.; North, M. Org. Lett. 2003, 5, 4505.
10. (g) Lundgren, S.; Wingstrand, E.; Penhoat, M.; Moberg, C. J. Am. Chem. Soc. 2005, 127, 11592.
11. (h) Belokon, Y. N.; Ishibashi, E.; Nombra, H.; North, M. Chem. Commun. 2006, 16, 1775.
12. (a) Dornow, A.; Lüpfert, S. Chem. Ber. 1956, 89, 2718.
13. (b) Dornow, A.; Lüpfert, S. Chem. Ber. 1957, 90, 1780.
14. (c) Dornow, A.; Lüpfert, S. US Patent 2849477, 1958.
15. (a) Gardent, M. J.; Delépine, M. M. C. R. Acad. Sci. 1958, 247, 2153.
16. (b) Rai, M.; Krishan, K.; Singh, A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1978, 16, 834.
17. (c) Sakamoto, M.; Akiyama, Y.; Furumi, N.; Ishii, K.; Tomimatsu, Y.; Date, T. Chem. Pharm. Bull. 1983, 31, 2623.
18. For reviews, see: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
19. (b) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
20. (c) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520.
21. (d) Connon, S. J. Chem. Eur. J. 2006, 12, 5418.
22. (e) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
23. (f) Connon, S. J. Angew. Chem. Int. Ed. 2006, 45, 3909.
24. Under our reaction conditions using triethylamine as the catalyst only 4% conversion of imine 1a to product 4a was achieved.
25. Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
26. (a) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217.
27. (b) Wittkopp, A.; Schreiner, P. R. Chem. Eur. J. 2003, 9, 407.
28. Even in the absence of catalyst, significant conversion (>30%) to the product was observed.
29. Using the chiral phosphoric acid catalyst 3,3′-bis[(2,4,6- tris(isopropyl)phenyl]-5,5′,6,6′,7,7′,8,8′-octahydro-1, 1-binaphthyl hydrogen phosphate (10 mol%) at -40 °C, product 4a was obtained in 92% yield and 69:31 er.