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Volumn 5, Issue 21, 2003, Pages 3899-3902

Lewis Acid-Mediated Reactions of Alkyl Azides with α,β- Unsaturated Ketones

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; KETONE DERIVATIVE; LEWIS ACID; TRIAZOLINE DERIVATIVE;

EID: 0242628713     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0355130     Document Type: Article
Times cited : (70)

References (53)
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    • Kyba, E.P.1
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    • Scriven, E.F.V.1    Turnbull, K.2
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    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
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    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
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    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
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    • Clive, D.L.J.1    Etkin, N.2
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    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
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    • Wang, Q.1    Chan, T.R.2    Hilgraf, R.3    Fokin, V.V.4    Sharpless, K.B.5    Finn, M.G.6
  • 9
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    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2113-2116
    • Demko, Z.P.1    Sharpless, K.B.2
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    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4011-4030
    • Evans, D.A.1    Britton, T.C.2    Ellman, J.A.3    Dorow, R.L.4
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    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5657-5660
    • Mertens, A.1    Lammertsma, K.2    Arvanaghi, M.3    Olah, G.A.4
  • 12
    • 0000650928 scopus 로고
    • For reviews and some recent leading references, see: (a) Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 397-440 (b) Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; John Wiley & Sons: London, 1971; pp 221-329. (c) Kyba, E. P. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 2-34. (d) Scriven, E. F. V. ; Turnbull, K. Chem. Rev. 1988, 88, 297-368. (e) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521-5522. (f) Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809-6813. (g) Clive, D. L. J.; Etkin, N. Tetrahedron Lett. 1994, 35, 2459-2462. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193. (i) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (j) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. (k) Mertens, A.; Lammertsma, K.; Arvanaghi, M.; Olah, G. A. J. Am. Chem. Soc. 1983, 105, 5657-5660. (l) Khouki, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031-1034.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1031-1034
    • Khouki, M.1    Vaultier, M.2    Carrié, R.3
  • 18
    • 0242678918 scopus 로고    scopus 로고
    • note
    • Coincidently, a single crystal of the minor isomer (E)-1 was picked from the mixture of E,Z isomers for X-ray analysis.
  • 52
    • 0242426988 scopus 로고    scopus 로고
    • note
    • Formation of aziridine 10 can be explained by the following mechanism.


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