The synthesis of functionalised β-hydroxyhydroxylamines via the ring opening of epoxides and their use in reverse cope cyclisations

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9089-9092

  O'Neil, Ian A ^a   Southern, J Mike ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; HYDROXYLAMINE; METHANOL; METHYL CHLORIDE; PIPERIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; HEATING; HYDROGEN BOND; HYDROXYLATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032480956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02001-2     Document Type: Article

References (23)

1. 1. I. A. O'Neil, N. D. Miller, J. Peake, J. V. Barkley, C. M. R. Low and S. B. Kalindjian, Synlett 1993, 515.
2. I. A. O'Neil, N. D. Miller, J. V. Barkley, C. M. R. Low and S. B. Kalindjian, Synlett 1995, 617 and 619.
3. I. A. O'Neil and A. J. Potter, Tetrahedron Lett. 1997, 38, 5731.
4. I. A. O'Neil, C. D. Turner and S. B. Kalindjian, Synlett 1997, 777.
5. I. A. O'Neil and A. J. Potter, J. Chem. Soc., Chem. Commun. 1998, 1487.
6. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
7. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
8. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
9. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
10. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
11. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
12. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
13. 2. M. B. Gravestock, D. W. Knight and S. R. Thornton, J. Chem. Soc., Chem. Commun. 1993, 169. K. E. Bell, M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8545. M. P. Coogan, M. B. Gravestock, D. W. Knight and S. R. Thornton, Tetrahedron Lett. 1997, 38, 8549. A. R. Wheildon, D. W. Knight and M. P. Leese, Tetrahedron Lett. 1997, 38, 8553. W. Oppolzer, A. C. Spivey and C. G. Bochet, J. Am. Chem. Soc. 1994, 116, 3139. E. Ciganek, J. Org. Chem. 1990, 55, 3007. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1 1994, 3379. E. Ciganek, J. M. Read, Jr and J. C. Calabrese, J. Org. Chem. 1995, 60, 5795 and 5803.
14. 3. P. D. Bailey, P. A. Millwood and P. D. Smith, Chem. Commun. 1998, 633. A. Pahl, R. Wartchow and H. H. Meyer, Tetrahedron Lett. 1998, 39, 2095. C. J. Moody, A. P. Lighlfoot and P.T. Gallagher, J. Org. Chem. 1997, 62, 746.
15. 3. P. D. Bailey, P. A. Millwood and P. D. Smith, Chem. Commun. 1998, 633. A. Pahl, R. Wartchow and H. H. Meyer, Tetrahedron Lett. 1998, 39, 2095. C. J. Moody, A. P. Lighlfoot and P.T. Gallagher, J. Org. Chem. 1997, 62, 746.
16. 3. P. D. Bailey, P. A. Millwood and P. D. Smith, Chem. Commun. 1998, 633. A. Pahl, R. Wartchow and H. H. Meyer, Tetrahedron Lett. 1998, 39, 2095. C. J. Moody, A. P. Lighlfoot and P.T. Gallagher, J. Org. Chem. 1997, 62, 746.
17. 4. S. R. Sandler and W. Karo, "Organic Functional Group Preparations" Academic Press, 1989, vol 3, 377-429. M. T. Reetz, D. Rohrig, K. Harms and G. Frenking, Tetrahedron Lett. 1994, 35, 8765. M. P. Sibi, J. J. Shay, M. Liu and C. P. Jasperse, J. Am. Chem. Soc., 1998, 120, 6615.
18. 4. S. R. Sandler and W. Karo, "Organic Functional Group Preparations" Academic Press, 1989, vol 3, 377-429. M. T. Reetz, D. Rohrig, K. Harms and G. Frenking, Tetrahedron Lett. 1994, 35, 8765. M. P. Sibi, J. J. Shay, M. Liu and C. P. Jasperse, J. Am. Chem. Soc., 1998, 120, 6615.
19. 4. S. R. Sandler and W. Karo, "Organic Functional Group Preparations" Academic Press, 1989, vol 3, 377-429. M. T. Reetz, D. Rohrig, K. Harms and G. Frenking, Tetrahedron Lett. 1994, 35, 8765. M. P. Sibi, J. J. Shay, M. Liu and C. P. Jasperse, J. Am. Chem. Soc., 1998, 120, 6615.
20. 5. S. Jordan, R. E. Markwell and B. S. Woolcott, J. Chem. Soc., Perkin 1 1978, 928. M. S. Malinovskii and V. A. Martyushenko, Chem. Abs. 1966, 64, 625. G. Zinner and A. W. Ritter, Angew. Chem. 1962, 74, 21.
21. 5. S. Jordan, R. E. Markwell and B. S. Woolcott, J. Chem. Soc., Perkin 1 1978, 928. M. S. Malinovskii and V. A. Martyushenko, Chem. Abs. 1966, 64, 625. G. Zinner and A. W. Ritter, Angew. Chem. 1962, 74, 21.
22. 5. S. Jordan, R. E. Markwell and B. S. Woolcott, J. Chem. Soc., Perkin 1 1978, 928. M. S. Malinovskii and V. A. Martyushenko, Chem. Abs. 1966, 64, 625. G. Zinner and A. W. Ritter, Angew. Chem. 1962, 74, 21.
23. 3 requires 198.11302, found 198.11332.