Hypervalent iodine chemistry: New oxidation reactions using the iodosylbenzene-trimethylsilyl azide reagent combination. Direct α- and β-azido functionalization of triisopropylsilyl enol ethers

Journal of the American Chemical Society

Volumn 118, Issue 14, 1996, Pages 3406-3418

  Magnus, Philip ^a   Lacour, Jérôme ^a   Evans, P Andrew ^a   Roe, Michael B ^a   Huhne, Christopher ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; TEMPERATURE;

EID: 0029915129     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953906r     Document Type: Article

References (74)

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45. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
46. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
47. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
48. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
49. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
50. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
51. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
52. For a review of redox chemistry using TEMPO, see: Yamaguchi, M., Miyazawa, T.; Takata, T., Endo, T. Pure Appl. Chem. 1990, 62, 217. Kinetics of the coupling of TEMPO with carbon-centered radicals: Beckwith, A. L. J., Bowry, V. W. J. Org. Chem. 1988, 53, 1632 TEMPO as an efficient radical trap. Barton, D. H. R.; Hill, D. R Tetrahedron Lett. 1994, 35, 1431. Barton, D H. R., Bévière, S. D., Chavasiri, W ; Csuhai, E., Doller, D , Liu, W.-G. J Am. Chem. Soc 1992, 114, 2147. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687. Bowry, V W , Lusztjk, J , Ingold, K. U J Am. Chem. Soc. 1989, 111, 1927 Chateauneuf, J., Lusztyk, J.; Engold, K. U. J Am. Chem Soc. 1988, 110, 2877. Chateauneuf, J.; Lusztyk, J., Ingold, K U. J. Org. Chem. 1988, 53, 1629 Evans, C. A. Aldrichimica Acta 1979, 12, 23. Keana, J. F. W Chem. Rev. 1978, 78, 37. TEMPO as a radical trap in hypervalent iodine chemistry: Togo, H.; Aoki, M ; Kuramochi, T , Yokohama, M J. Chem. Soc , Perkin Trans. 1 1993, 2417.
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