Copper(II)-catalyzed [2,3]-sigmatropic rearrangement of N-methyltetrahydropyridinium ylids

Journal of Organic Chemistry

Volumn 68, Issue 10, 2003, Pages 4083-4086

  Heath, Peter ^a   Roberts, Edward ^b   Sweeney, Joseph B ^a   Wessel, Hans Peter ^b   Workman, James A ^a  

^a UNIVERSITY OF READING   (United Kingdom)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER; RHODIUM; SALTS;

SIGMATROPIC REARRANGEMENT;

ORGANIC COMPOUNDS;

1,2,3,6 TETRAHYDRO 1 METHYLPYRIDINE; COPPER COMPLEX; DIAZOACETIC ACID ETHYL ESTER; ETHYL 3 AZA 3 METHYLOCTA 5,7 DIENOATE; ETHYL N METHYL 3 ETHENYLPROLINE; METAL COMPLEX; N METHYL 2 ETHOXYCARBONYL 3 ETHENYLPYRROLIDINE; N METHYLTETRAHYDROPYRIDINIUM YLIDE; PROLINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

EID: 0038626783     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034147v     Document Type: Article

References (16)

1. Burns, B.; Coates, B.; Neeson, S.; Stevenson, P. J. Tetrahedron Lett. 1990, 31, 4351. Neeson, S. J.; Stevenson, P. J. Tetrahedron Lett. 1988, 29, 3993.
2. Burns, B.; Coates, B.; Neeson, S.; Stevenson, P. J. Tetrahedron Lett. 1990, 31, 4351. Neeson, S. J.; Stevenson, P. J. Tetrahedron Lett. 1988, 29, 3993.
3. For original reports of onium ylid rearrangements, see: Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Am. Chem. Soc. 1968, 90, 4758. Blackburn, G. M.; Ollis, W. D.; Smith, C.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1968, 168. Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Chem. Soc., Chem. Commun. 1968, 537, 538.
4. For original reports of onium ylid rearrangements, see: Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Am. Chem. Soc. 1968, 90, 4758. Blackburn, G. M.; Ollis, W. D.; Smith, C.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1968, 168. Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Chem. Soc., Chem. Commun. 1968, 537, 538.
5. For original reports of onium ylid rearrangements, see: Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Am. Chem. Soc. 1968, 90, 4758. Blackburn, G. M.; Ollis, W. D.; Smith, C.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1968, 168. Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Chem. Soc., Chem. Commun. 1968, 537, 538.
6. Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113.
7. For a review of biological significance see: Excitatory Amino Acids in Health and Disease; Lodge, D., Ed.; J. Wiley & Sons: New York, 1988. Kainic Acid as a Tool in Neurobiology; McGeer, E. G., Olney, J. W., McGeer, P. L., Eds.; Raven Press: New York, 1978.
8. For a review of biological significance see: Excitatory Amino Acids in Health and Disease; Lodge, D., Ed.; J. Wiley & Sons: New York, 1988. Kainic Acid as a Tool in Neurobiology; McGeer, E. G., Olney, J. W., McGeer, P. L., Eds.; Raven Press: New York, 1978.
9. For a review of synthetic studies see: Parsons, A. F. Tetrahedron 1996, 52, 4149. Synthesis of Optically Active α-Amino Acids; Williams, R. M., Ed.; Pergamon Press: New York, 1989.
10. For a review of synthetic studies see: Parsons, A. F. Tetrahedron 1996, 52, 4149. Synthesis of Optically Active α-Amino Acids; Williams, R. M., Ed.; Pergamon Press: New York, 1989.
11. Doyle, M. P.; Tamblyn, W. H.; Bagheri, V. J. Org. Chem. 1981, 46, 5094.
12. Doyle, M. P. Chem. Rev. 1986, 86, 919.
13. Carpes, M. J.; Miranda, P. C.; Correia, C. R. Tetrahedron Lett. 1997, 38, 1869.
14. (a) Mageswaran, S.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1981, 1953.
15. (b) Mageswaran, S.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1973, 656.
16. Alonso, M. E.; Fernandez, R. Tetrahedron 1989, 45, 3313.