Reaction of silyldihalomethyllithiums with nitriles: Formation of α-keto acylsilanes via azirines and 1,3-rearrangement of silyl group from C to N

Journal of the American Chemical Society

Volumn 126, Issue 28, 2004, Pages 8618-8619

  Yagi, Kazunari ^a   Tsuritani, Takayuki ^a   Takami, Kazuaki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA KETO ACYLSILANE; LITHIUM DERIVATIVE; NITRILE; SILANE DERIVATIVE; SILYLDIHALOMETHYLLITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL COMPOSITION; ELECTRON; PROTON TRANSPORT; REACTION ANALYSIS; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

EID: 3242693081     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047708o     Document Type: Article

References (24)

1. (a) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
2. (b) Moser, W. H. Tetrahedron 2001, 57, 2065-2084 and references therein.
3. (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954.
4. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514.
5. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462.
6. (a) Smith, A. B., III; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925-6926.
7. (b) Smith, A. B., III; Pitram, S. M.; Boldi, A. M.; Gaunt, M. J.; Sfouggatakis, C.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 14435-14445.
8. (a) Fuji, K.; Ueda, M.; Sumi, K.; Fujita, E. J. Org. Chem. 1985, 50, 662-666.
9. (b) Lappert, M. F.; Liu, D.-S. J. Organomet. Chem. 1995, 500, 203-217.
10. (c) Honda, T.; Mori, M. J. Org. Chem. 1996, 61, 1196-1197.
11. (d) Bulman Page, P. C.; van Niel, M. B.; Westwood, D. J. Chem. Soc., Perkin Trans. 1 1988, 269-275.
12. (e) Cunico, R. F.; Kuan, C. P. J. Org. Chem. 1992, 57, 3331-3336.
13. (a) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195.
14. (b) Ricci, A.; Degl'Innocent, A. Synthesis 1989, 647-666.
15. (c) Cirillo, P. F.; Panek, J. S. Org. Prep. Proced. Int. 1992, 24, 555-582.
16. (a) Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949-960.
17. (b) Page, P. C. B.: Rosenthal, S. Tetrahedron 1990, 46, 2573-2586.
18. (a) Pinho e Melo, T. M. V. D.; Lopes, C. S. J.; Cardoso, A. L.; Rocha Gonsalves, A. M. d'A. Tetrahedron 2001, 57, 6203-6208.
19. (b) Pinho e Melo, T. M. V. D.; Lopes, C. S. J.; Rocha Gonsalves, A. M. d'A.; Beja, A. M.; Paixao, J. A.; Silva, M. R.; Luiz Alte de Veiga J. Org. Chem. 2002, 67, 66-71.
20. (c) Padwa, A.; Blacklock, T. J.; Carlsen, P. H. J.; Pulwer, M. J. Org. Chem. 1979, 44, 3281-3287.
21. (d) Gallagher, T. C.; Storr, R. C. Tetrahedron Lett. 1981, 22, 2905-2908.
22. (e) Gallagher, T. C.; Storr, R. C. Tetrahedron Lett. 1981, 22, 2909-2912.
23. Katritzky, A. R.; Wang, M.; Wilkerson, C. R.; Yang, H. J. Org. Chem. 2003, 68, 9105-9108. See also ref 7b.
24. The addition of HMPA did not improve the yield of 13a.