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Volumn 68, Issue 17, 2003, Pages 6497-6501

Strategies for the design of organic aziridination reagents and catalysts: Transition structures for alkene aziridinations by NH transfer

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CATALYSTS; ELECTRONS; NITROGEN;

EID: 0043011226     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034415p     Document Type: Article
Times cited : (17)

References (39)
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    • For representative papers discussing alkene aziridinations using inorganic catalysts see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. (b) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sherpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. (c) Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1998, 54, 13485. (d) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5226. (e) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30. (f) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450. (g) Liang, J.; Huang, J.; Yu, X.; Zhu, N.; Che, C. Chem. Eur. J. 2002, 8, 1563.
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    • For representative papers discussing alkene aziridinations using inorganic catalysts see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. (b) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sherpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. (c) Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1998, 54, 13485. (d) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5226. (e) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30. (f) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450. (g) Liang, J.; Huang, J.; Yu, X.; Zhu, N.; Che, C. Chem. Eur. J. 2002, 8, 1563.
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    • For representative papers discussing alkene aziridinations using inorganic catalysts see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. (b) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sherpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. (c) Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1998, 54, 13485. (d) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5226. (e) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30. (f) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450. (g) Liang, J.; Huang, J.; Yu, X.; Zhu, N.; Che, C. Chem. Eur. J. 2002, 8, 1563.
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    • 0035847220 scopus 로고    scopus 로고
    • For representative papers discussing alkene aziridinations using inorganic catalysts see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. (b) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sherpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. (c) Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1998, 54, 13485. (d) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5226. (e) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30. (f) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450. (g) Liang, J.; Huang, J.; Yu, X.; Zhu, N.; Che, C. Chem. Eur. J. 2002, 8, 1563.
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    • 0037123608 scopus 로고    scopus 로고
    • For representative papers discussing alkene aziridinations using inorganic catalysts see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. (b) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sherpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. (c) Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1998, 54, 13485. (d) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5226. (e) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30. (f) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450. (g) Liang, J.; Huang, J.; Yu, X.; Zhu, N.; Che, C. Chem. Eur. J. 2002, 8, 1563.
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    • Gillespie, K.M.1    Sanders, C.J.2    O'Shaughnessy, P.3    Westmoreland, I.4    Thickitt, C.P.5    Scott, P.6
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    • For representative papers discussing alkene aziridinations using inorganic catalysts see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. (b) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sherpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. (c) Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1998, 54, 13485. (d) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5226. (e) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30. (f) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450. (g) Liang, J.; Huang, J.; Yu, X.; Zhu, N.; Che, C. Chem. Eur. J. 2002, 8, 1563.
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    • (a) For a review see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. For the synthesis of chiral NH-oxaziridines see: (b) Limousin, C.; Murrell, V. L. J. Org. Chem. 2002, 67, 7787. (c) Page, P. C. B.; Murrell, V. L. ; Limousin, C.; Laffan, D. D. P.; Bethell, D.; Slawin, A. M. Z.; Smith, T. A. D. J. Org. Chem. 2000, 65, 4204.
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    • (a) For a review see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. For the synthesis of chiral NH-oxaziridines see: (b) Limousin, C.; Murrell, V. L. J. Org. Chem. 2002, 67, 7787. (c) Page, P. C. B.; Murrell, V. L. ; Limousin, C.; Laffan, D. D. P.; Bethell, D.; Slawin, A. M. Z.; Smith, T. A. D. J. Org. Chem. 2000, 65, 4204.
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    • For reviews on related diaziridines see: (a) Schmitz, E. Chem. Ber. 1962, 95, 676. (b) Schmitz, E. Angew. Chem., Int. Ed. 1964, 3, 333. (c) Schmitz, E. Advances in Heterocyclic Chemistry; Academic Press: New York, 1963; Vol. 2, pp 83-130.
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