β-metallation of bridged alkenyl sulfones: Access to a key intermediate for epibatidine total synthesis

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 1021-1022

  Jones, Clifford D ^a   Simpkins, Nigel S ^a   Giblin, Gerard M P ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKENYL GROUP; EPIBATIDINE; SULFONE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032568126     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10692-X     Document Type: Article

References (11)

1. 1. For the most recent work, see Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem Soc., Chem. Commun. 1997, 1857.
2. 2. Giblin, G. M. P.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
3. 3. See accompanying paper for preliminary results of the enantioselective elimination reaction.
4. 4. The apparent alternative, involving the use of an alkenyl bis-sulfone is not viable because these compounds do not undergo cycloaddition with pyrrole partners.
5. 5. Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177.
6. 6. Riera, A.; Marti, M.; Moyano, A.; Pericas, M. A.; Santamaria, J. Tetrahedron Lett. 1990, 31, 2173.
7. 7. De Lucchi, O.; Cossu, S. J. Chem. Soc., Chem. Commun. 1992, 1089.
8. 8. (a) Barton, D. L.; Conrad, P. C.; Fuchs, P. L. Tetrahedron Lett. 1980, 21, 1811.
9. (b) Cassidy, J. F.; Williams, J. M. Tetrahedron Lett. 1986, 27, 4355.
10. (c) Fuchs, P. L.; Braish, T. F. Chem Rev. 1986, 903.
11. 9. For a review of sulfone metallations, see Simpkins, N. S. Sulfones in Organic Synthesis, Pergamon Press, 1993.