A mild and efficient cyanosilylation of ketones catalyzed by a Lewis acid-Lewis base bifunctional catalyst

Tetrahedron

Volumn 59, Issue 30, 2003, Pages 5667-5675

  Shen, Yongcun ^b   Feng, Xiaoming ^a   Li, Yan ^a   Zhang, Guolin ^c   Jiang, Yaozhong ^b  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

Catalyst; Cyanosilylation; Ketone; Lewis acid; Lewis base

Indexed keywords

1 (2' PYRIDYLMETHYL) 2 DIPHENYLHYDROXYMETHYLPYRROLIDINE N OXIDE TITANIUM; KETONE DERIVATIVE; LEWIS ACID; N BENZYL DIETHANOLAMINE N OXIDE TITANIUM; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SILYLATION; STEREOCHEMISTRY;

EID: 0037630662     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00908-6     Document Type: Article

References (43)

1. (a) Gregory R.J.H. Chem. Rev. 99:1999;3649-3682
2. (b) Matthews B.R., Gountzos H., Jackson W.R., Watson K.G. Tetrahedron Lett. 30:1989;5157-5160
3. (c) Jackson W.R., Jacobs H.A., Jayatilake G.S., Matthews B.R., Watson K.G. Aust. J. Chem. 43:1990;2045-2048
4. (d) Jackson W.R., Jacobs H.A., Matthews B.R., Jayatilake G.S., Watson K.G. Tetrahedron Lett. 31:1990;1447-1451
5. (e) Ziegler T., Horsch B., Effenberger F. Synthesis. 1990;575-578
6. (f) Effenberger F., Stelzer U. Angew. Chem. Int. Ed. Engl. 30:1991;873-874
7. (g) Zandbergen P., Brussee J., Van der Gen A., Kruse C.G. Tetrahedron: Asymmetry. 3:1992;769-773. and references therein cited
8. (h) Griengl H., Hickel A., Johnson D.V., Kratky C., Schmidt M., Schwab H. Chem. Commun. 1997;1933-1940. and references therein cited.
9. (a) Evans D.A., Truesdale L.K., Carroll G.L. J. Chem. Soc., Chem. Commun. 1973;55-58
10. (b) Gassman P.G., Talley J.J. Tetrahedron Lett. 19:1978;3773-3776
11. (c) Noyori R., Murato S., Suzuki M. Tetrahedron. 37:1981;3899-3910
12. (d) Reetz M.T., Drewes M.W., Harms K., Reif W. Tetrahedron Lett. 29:1988;3295-3298
13. (e) Singh V.K., Saravanan P., Anand R.V. Tetrahedron Lett. 39:1998;3823-3824
14. (f) Wilkinson H.S., Grover P.T., Vandenbossche C.P., Bakale R.P., Bhongle N.N., Wald S.A., Senanayake C.H. Org. Lett. 3:2001;553-556
15. (g) Bandini M., Cozzi P.G., Melchiorre P., Umani-Ronchi A. Tetrahedron Lett. 42:2001;3041-3043. and references therein cited
16. (h) North M. Synlett. 1993;807-820. and references therein cited.
17. (a) Corey E.J., Guzman-Perez A. Angew. Chem. Int. Ed. 37:1998;380-401
18. (b) Fuji K. Chem. Rev. 93:1993;2037-2066
19. (c) Dosa P.I., Fu G.C. J. Am. Chem. Soc. 120:1998;445-446.
20. (a) Corey E.J., Shibata S. J. Am. Chem. Soc. 109:1987;5551-5553
21. (b) Kitamura M., Suga S., Niwa M., Noyori R. J. Am. Chem. Soc. 117:1995;4832-4842
22. (c) Shibasaki M., Sasai H., Arai T. Angew. Chem. Int. Ed. Engl. 36:1997;1236-1256
23. (d) Kim Y.S., Matsunaga S., Das J., Sekine A., Oshima T., Shibasaki M. J. Am. Chem. Soc. 122:2000;6506-6507. and references therein
24. (e) Gample M.P., Smith A.R.C., Wills M. J. Org. Chem. 63:1998;6068-6071
25. (f) Yamakawa M., Ito H., Noyori R. J. Am. Chem. Soc. 122:2000;1466-1478. and references therein
26. (g) Trost B.M., Ito H. J. Am. Chem. Soc. 122:2004;12003-12004
27. (h) List B., Pojarliev P., Castello C. Org. Lett. 3:2001;573-575. and references therein.
28. (a) Sawamura M., Ito Y. Chem. Rev. 92:1992;857-871
29. (b) van den Beuken E.K., Feringa B.L. Tetrahedron. 54:1998;12985-13011
30. (c) Rowland G.J. Tetrahedron. 57:2001;1865-1882.
31. (a) Hamashima Y., Sawada D., Kani M., Shibasaki M. J. Am. Chem. Soc. 121:1999;2641-2642
32. (b) Hamashima Y., Sawada D., Nogami H., Kanai M., Shibasaki M. Tetrahedron. 57:2001;805-814
33. (c) Hamashima Y., Kani M., Shibasaki M. J. Am. Chem. Soc. 122:2000;7412-7413.
34. Casas J., Najera C., Sansano J.M., Saá J.M. Org. Lett. 4:2002;2589-2592.
35. Hamashima Y., Kanai M., Shibasaki M. J. Am. Chem. Soc. 122:2000;7412-7413.
36. (a) Liu B., Feng X.-M., Chen F.-X., Zhang G.-L., Cui X., Jiang Y.-Z. Synlett. 2001;1551-1554
37. (b) Sato K., Kira M., Sakurai H. Tetrahedron Lett. 30:1989;4375-4377.
38. Shen Y.-C., Feng X.-M., Li Y., Zhang G.-L., Jiang Y.-Z. Synlett. 2002;793-795.
39. (a) Chelucci, Giorgio, Falorni, Massimo, Giacomelli, Giampaolo. Tetrahedron: Asymmetry. 1:1990;843-849
40. (b) O'Neil I.A., Miller N.D., Barkley J.V., Low C.M.R., Kalindjian S.B. Synlett. 1995;617-619.
41. Kobayashi S., Tsuchiya Y., Mukaiyama T. Chem. Lett. 1991;537-540.
42. (a) Coles S.J., Hursthouse M.B., Kelly D.G., Toner A.J., Walker N.M. J. Chem. Soc., Dalton Trans. 1998;3489-3494
43. (b) Josephsohn N.S., Kuntz K.W., Snapper M.L., Hoveyda A.H. J. Am. Chem. Soc. 123:2001;11594-11599.