Synthesis of O-alkylhydroxylamines by electrophilic amination of alkoxides

Chemical Communications

Volumn , Issue 11, 2000, Pages 975-976

  Foot, Oliver F ^a   Knight, David W ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLAMINE; LITHIUM DERIVATIVE;

AMINATION; ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034616753     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002388o     Document Type: Article

References (27)

1. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915; S. P. Bew and D. W. Knight, Chem. Commun., 1996, 1007; A. D. Jones, D. W. Knight, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 1999, 40, 3267; S. B. Bedford, K. E. Bell, F. Bennett, C. J. Hayes, D. W. Knight and D. E. Shaw, J. Chem. Soc., Perkin Trans. 1, 1999, 2143.
2. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915; S. P. Bew and D. W. Knight, Chem. Commun., 1996, 1007; A. D. Jones, D. W. Knight, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 1999, 40, 3267; S. B. Bedford, K. E. Bell, F. Bennett, C. J. Hayes, D. W. Knight and D. E. Shaw, J. Chem. Soc., Perkin Trans. 1, 1999, 2143.
3. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915; S. P. Bew and D. W. Knight, Chem. Commun., 1996, 1007; A. D. Jones, D. W. Knight, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 1999, 40, 3267; S. B. Bedford, K. E. Bell, F. Bennett, C. J. Hayes, D. W. Knight and D. E. Shaw, J. Chem. Soc., Perkin Trans. 1, 1999, 2143.
4. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915; S. P. Bew and D. W. Knight, Chem. Commun., 1996, 1007; A. D. Jones, D. W. Knight, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 1999, 40, 3267; S. B. Bedford, K. E. Bell, F. Bennett, C. J. Hayes, D. W. Knight and D. E. Shaw, J. Chem. Soc., Perkin Trans. 1, 1999, 2143.
5. O. Mitsunobu, Synthesis, 1981, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 65; D. L. Hughes, Org. React., 1992, 42, 335; D. L. Hughes, Org. Prep. Proced. Int., 1996, 28, 127.
6. O. Mitsunobu, Synthesis, 1981, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 65; D. L. Hughes, Org. React., 1992, 42, 335; D. L. Hughes, Org. Prep. Proced. Int., 1996, 28, 127.
7. O. Mitsunobu, Synthesis, 1981, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 65; D. L. Hughes, Org. React., 1992, 42, 335; D. L. Hughes, Org. Prep. Proced. Int., 1996, 28, 127.
8. O. Mitsunobu, Synthesis, 1981, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 65; D. L. Hughes, Org. React., 1992, 42, 335; D. L. Hughes, Org. Prep. Proced. Int., 1996, 28, 127.
9. O. Mitsunobu, Synthesis, 1981, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 1; O. Mitsunobu, Comp. Org. Synth, 1991, 6, 65; D. L. Hughes, Org. React., 1992, 42, 335; D. L. Hughes, Org. Prep. Proced. Int., 1996, 28, 127.
10. E. Breuer, H. G. Aurich and A. Nielsen, Nitrones, Nitronates and Nitroxides, ed. S. Patai and Z. Rappoport, John Wiley and Sons, Chichester, 1989.
11. E. Grochowski and J. Jurczak, Synthesis, 1976, 682. We found that ethyl acetate was a superior solvent for this reaction; see: H. Iwagami, M. Yatagi, M. Nakazawa, H. Orita, Y. Honda, T. Ohnuki and T. Yukawa, Bull. Chem. Soc. Jpn., 1991, 64, 175.
12. E. Grochowski and J. Jurczak, Synthesis, 1976, 682. We found that ethyl acetate was a superior solvent for this reaction; see: H. Iwagami, M. Yatagi, M. Nakazawa, H. Orita, Y. Honda, T. Ohnuki and T. Yukawa, Bull. Chem. Soc. Jpn., 1991, 64, 175.
13. M. Fujimoto and M. Sakai, Chem. Pharm. Bull., 1965, 13, 248.
14. O. F. Foot and D.W. Knight, in preparation.
15. For recent notable contributions, see: S. D. Bull, S. G. Davies, S. Jones, J. V. A. Ouzman, A. J. Price and D. J. Watkin, Chem. Commun., 1999, 2079; Y.-M. Lm and M. J. Miller, J. Org. Chem., 1999, 64, 7451.
16. For recent notable contributions, see: S. D. Bull, S. G. Davies, S. Jones, J. V. A. Ouzman, A. J. Price and D. J. Watkin, Chem. Commun., 1999, 2079; Y.-M. Lin and M. J. Miller, J. Org. Chem., 1999, 64, 7451.
17. J. Vidal, S. Damestoy, L. Guy, J.-C. Hannachi, A. Aubry and A. Collet, Chem. Eur. J., 1997, 3, 1691; J. Vidal, J.-C. Hannachi, G. Hourdin, J.-C. Mulatier and A. Collet, Tetrahedron Lett., 1998, 39, 8845 and references cited therein.
18. J. Vidal, S. Damestoy, L. Guy, J.-C. Hannachi, A. Aubry and A. Collet, Chem. Eur. J., 1997, 3, 1691; J. Vidal, J.-C. Hannachi, G. Hourdin, J.-C. Mulatier and A. Collet, Tetrahedron Lett., 1998, 39, 8845 and references cited therein.
19. F. A. Davis and A. C. Sheppard, Tetrahedron, 1989, 45, 5703; F. A. Davis and B.-C Chen, Chem. Rev., 1992, 92, 912.
20. F. A. Davis and A. C. Sheppard, Tetrahedron, 1989, 45, 5703; F. A. Davis and B.-C Chen, Chem. Rev., 1992, 92, 912.
21. W. Theilacker and K. Ebke, Angew. Chem., 1956, 68, 303. For a review of electrophilic amination in general, see: S. Andreae and E. Schmitz, Synthesis, 1991, 327.
22. W. Theilacker and K. Ebke, Angew. Chem., 1956, 68, 303. For a review of electrophilic amination in general, see: S. Andreae and E. Schmitz, Synthesis, 1991, 327.
23. I. C. Choong and J. A. Ellman, J. Org. Chem., 1999, 64, 6528.
24. Satisfactory spectroscopic and analytic data have been obtained for all compounds reported herein.
25. For examples of Boc hydrolysis in such hydroxylamine derivates, see, for example, L. A. Carpino, C. A. Giza and B. A. Carpino, J. Am. Chem. Soc., 1959, 81, 955; T. Sheradsky, G. Salemnick and Z. Nir, Tetrahedron, 1972, 28, 3833; C. Baloli, P. D. Buttero, E. Licandro and S. Mairona, Synthesis, 1988, 344.
26. For examples of Boc hydrolysis in such hydroxylamine derivates, see, for example, L. A. Carpino, C. A. Giza and B. A. Carpino, J. Am. Chem. Soc., 1959, 81, 955; T. Sheradsky, G. Salemnick and Z. Nir, Tetrahedron, 1972, 28, 3833; C. Baloli, P. D. Buttero, E. Licandro and S. Mairona, Synthesis, 1988, 344.
27. For examples of Boc hydrolysis in such hydroxylamine derivates, see, for example, L. A. Carpino, C. A. Giza and B. A. Carpino, J. Am. Chem. Soc., 1959, 81, 955; T. Sheradsky, G. Salemnick and Z. Nir, Tetrahedron, 1972, 28, 3833; C. Baloli, P. D. Buttero, E. Licandro and S. Mairona, Synthesis, 1988, 344.