Intramolecular cyclisations of hydroxylamines derived from limonene: Reverse-Cope or acid-catalysed reactions?

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6417-6420

  Coogan, Michael P ^a   Knight, David W ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030603083     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01362-7     Document Type: Article

References (25)

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14. 5. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R. and Wilkes, B.E. J. Org. Chem., 1976, 41, 855; House, H.O. and Lee, L.F. J. Org. Chem., 1976, 41, 863; Black, D.St.C. and Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H. and Petrzilka, M. Tetrahedron Lett., 1979, 4391.
15. 5. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R. and Wilkes, B.E. J. Org. Chem., 1976, 41, 855; House, H.O. and Lee, L.F. J. Org. Chem., 1976, 41, 863; Black, D.St.C. and Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H. and Petrzilka, M. Tetrahedron Lett., 1979, 4391.
16. 5. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R. and Wilkes, B.E. J. Org. Chem., 1976, 41, 855; House, H.O. and Lee, L.F. J. Org. Chem., 1976, 41, 863; Black, D.St.C. and Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H. and Petrzilka, M. Tetrahedron Lett., 1979, 4391.
17. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
18. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
19. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
20. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
21. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
22. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
23. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
24. 6. Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E., Read, J.M. and Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Oppolzer, W.; Spivey, A.C. and Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Davison, E.C.; Holmes, A.B. and Forbes, I.T. Tetrahedron Lett, 1995, 36, 9047; Fox, M.E.; Holmes, A.B.; Forbes, I.T. and Thompson, M. J. Chem. Soc., Perkin Trans. 1, 1994, 3379; Gravestock, M.B.; Knight, D.W. and Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169; Leeson, P.D.; James, K. and Baker, R. J. Chem. Soc., Chem. Commun., 1989, 433; Karady, S.; Corley, E.G.; Abramson, N.L. and Weinstock, L.M. Tetrahedron Lett., 1989, 30, 2191 and references cited therein.
25. 7. Spectroscopic and analytical data fully support all the structures reported herein.