Synthesis of silyl aziridines and α-amino acylsilanes with silyldibromomethyllithium

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4339-4341

  Yagi, Kazunari ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM HYDROXIDE; AZIRIDINE DERIVATIVE; BROMINE DERIVATIVE; LITHIUM; LITHIUM DERIVATIVE; SILANE DERIVATIVE; WATER;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; GRIGNARD REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 9444295903     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048092a     Document Type: Article

References (32)

1. (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
2. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
3. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
4. (d) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: Oxford, 1996; Vol. 1A, p 1.
5. (a) Remers, W. A. The Chemistry of Antitumour Antibiotics; Wiley-Interscience: 1979; Vol. 1, p 242.
6. (b) Remers, W. A.; Dorr, R. T. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1988; Vol. 6, p 1.
7. (a) Aggarwal, V. K.; Ferrara, M. Org. Lett. 2000, 2, 4107.
8. (b) Aggarwal, V. K.; Alonso, E.; Ferrara, M.; Spey, S. E. J. Org. Chem. 2002, 67, 2335 and references therein. See also: Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1999, 2293.
9. (b) Aggarwal, V. K.; Alonso, E.; Ferrara, M.; Spey, S. E. J. Org. Chem. 2002, 67, 2335 and references therein. See also: Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1999, 2293.
10. (a) Bonini, B. F.; Comes-Franchini, M.; Mazzanti, G.; Ricci, A.; Sala, M. J. Org. Chem. 1996, 61, 7242.
11. (b) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Gawronsky, J.; Mazzanti, G.; Ricci, A.; Varchi, G. Eur. J. Org. Chem. 1999, 437.
12. (c) Bonini, B. F.; Comes-Franchini, M.; Mazzanti, G.; Passamonti, U.; Ricci, A.; Zani, P. Synthesis 1995, 92.
13. (d) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricci, A.; Varchi, G. Polyhedron 2000, 19, 529.
14. (a) Dibromomethylsilanes are easily prepared according to the reported procedure. Bacquet, C.; Masure, D.; Normant, J. F. Bull. Soc. Chim. Fr. 1975, 1797.
15. (b) Yoon, K.; Son, D. Y. J. Organomet. Chem. 1997, 545, 185
16. For the use of silyldihalomethyllithiums, see: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462. (d) Shinokubo, H.; Kondo, J.; Inoue, A.; Oshima, K. Chirality 2003, 15, 31. (e) Kondo, J. Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106. (g) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730 (h) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085.
17. For the use of silyldihalomethyllithiums, see: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462. (d) Shinokubo, H.; Kondo, J.; Inoue, A.; Oshima, K. Chirality 2003, 15, 31. (e) Kondo, J. Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106. (g) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730 (h) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085.
18. For the use of silyldihalomethyllithiums, see: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462. (d) Shinokubo, H.; Kondo, J.; Inoue, A.; Oshima, K. Chirality 2003, 15, 31. (e) Kondo, J. Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106. (g) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730 (h) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085.
19. For the use of silyldihalomethyllithiums, see: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462. (d) Shinokubo, H.; Kondo, J.; Inoue, A.; Oshima, K. Chirality 2003, 15, 31. (e) Kondo, J. Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106. (g) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730 (h) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085.
20. For the use of silyldihalomethyllithiums, see: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462. (d) Shinokubo, H.; Kondo, J.; Inoue, A.; Oshima, K. Chirality 2003, 15, 31. (e) Kondo, J. Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106. (g) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730 (h) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085.
21. For the use of silyldihalomethyllithiums, see: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462. (d) Shinokubo, H.; Kondo, J.; Inoue, A.; Oshima, K. Chirality 2003, 15, 31. (e) Kondo, J. Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106. (g) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730 (h) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085.
22. For the use of silyldihalomethyllithiums, see: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951-1954. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514. (c) Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 461-462. (d) Shinokubo, H.; Kondo, J.; Inoue, A.; Oshima, K. Chirality 2003, 15, 31. (e) Kondo, J. Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106. (g) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730 (h) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085.
23. For the synthesis of aziridines via the addition of lithium carbenoids to imines, see: (a) Deyrup, J. A.; Greenwald, R. B. J. Am. Chem. Soc. 1965, 87, 4538. (b) Deyrup, J. A.; Greenwald, R. B. Tetrahedron Lett. 1965, 6, 321. (c) Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Tetrahedron Lett. 1984, 25, 1949. (d) Chulabhorn, M.; Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Chem. Lett. 1984, 6, 969. (e) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631. (f) Davis, F. A.; Liu, H.; Zhou, P.; Fang, T. N.; Reddy, G. V.; Zhang, Y. L. J. Org. Chem. 1999, 64, 7559.
24. For the synthesis of aziridines via the addition of lithium carbenoids to imines, see: (a) Deyrup, J. A.; Greenwald, R. B. J. Am. Chem. Soc. 1965, 87, 4538. (b) Deyrup, J. A.; Greenwald, R. B. Tetrahedron Lett. 1965, 6, 321. (c) Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Tetrahedron Lett. 1984, 25, 1949. (d) Chulabhorn, M.; Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Chem. Lett. 1984, 6, 969. (e) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631. (f) Davis, F. A.; Liu, H.; Zhou, P.; Fang, T. N.; Reddy, G. V.; Zhang, Y. L. J. Org. Chem. 1999, 64, 7559.
25. For the synthesis of aziridines via the addition of lithium carbenoids to imines, see: (a) Deyrup, J. A.; Greenwald, R. B. J. Am. Chem. Soc. 1965, 87, 4538. (b) Deyrup, J. A.; Greenwald, R. B. Tetrahedron Lett. 1965, 6, 321. (c) Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Tetrahedron Lett. 1984, 25, 1949. (d) Chulabhorn, M.; Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Chem. Lett. 1984, 6, 969. (e) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631. (f) Davis, F. A.; Liu, H.; Zhou, P.; Fang, T. N.; Reddy, G. V.; Zhang, Y. L. J. Org. Chem. 1999, 64, 7559.
26. For the synthesis of aziridines via the addition of lithium carbenoids to imines, see: (a) Deyrup, J. A.; Greenwald, R. B. J. Am. Chem. Soc. 1965, 87, 4538. (b) Deyrup, J. A.; Greenwald, R. B. Tetrahedron Lett. 1965, 6, 321. (c) Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Tetrahedron Lett. 1984, 25, 1949. (d) Chulabhorn, M.; Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Chem. Lett. 1984, 6, 969. (e) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631. (f) Davis, F. A.; Liu, H.; Zhou, P.; Fang, T. N.; Reddy, G. V.; Zhang, Y. L. J. Org. Chem. 1999, 64, 7559.
27. For the synthesis of aziridines via the addition of lithium carbenoids to imines, see: (a) Deyrup, J. A.; Greenwald, R. B. J. Am. Chem. Soc. 1965, 87, 4538. (b) Deyrup, J. A.; Greenwald, R. B. Tetrahedron Lett. 1965, 6, 321. (c) Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Tetrahedron Lett. 1984, 25, 1949. (d) Chulabhorn, M.; Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Chem. Lett. 1984, 6, 969. (e) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631. (f) Davis, F. A.; Liu, H.; Zhou, P.; Fang, T. N.; Reddy, G. V.; Zhang, Y. L. J. Org. Chem. 1999, 64, 7559.
28. For the synthesis of aziridines via the addition of lithium carbenoids to imines, see: (a) Deyrup, J. A.; Greenwald, R. B. J. Am. Chem. Soc. 1965, 87, 4538. (b) Deyrup, J. A.; Greenwald, R. B. Tetrahedron Lett. 1965, 6, 321. (c) Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Tetrahedron Lett. 1984, 25, 1949. (d) Chulabhorn, M.; Reutrakul, V.; Prapansiri, V.; Panyachotipun, C. Chem. Lett. 1984, 6, 969. (e) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631. (f) Davis, F. A.; Liu, H.; Zhou, P.; Fang, T. N.; Reddy, G. V.; Zhang, Y. L. J. Org. Chem. 1999, 64, 7559.
29. 1,3-Rearrangement of a silyl group has been observed in the reaction of silyldichloromethyllithium with aromatic nitriles; see: Yagi, K.; Tsuritani, T.; Takami, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2004, 126, 8618.
30. (a) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195.
31. (b) Ricci, A.; Degl'Innocent, A. Synthesis 1989, 647-666.
32. Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 555-582.