Selenocyclisations of homoallylic sulfonamides: A highly stereoselective route to both cis- and trans-2,5-dihydropyrroles

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3267-3270

  Jones, Andrew D ^a   Knight, David W ^a,b   Redfern, Adele L ^b   Gilmore, Jeremy ^c  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

Cyclisation; Pyrrolidines; Selenonium ions; Sulfonamides

Indexed keywords

PYRROLE DERIVATIVE; SULFONAMIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; PHYSICAL CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033574452     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00380-9     Document Type: Article

References (14)

1. Jones, A D., Knight, D. W. Chem. Commun., 1996, 915.
2. Baldwin, J. E. J. Chem. Soc., Chem. Commun, 1976, 734, 738; Baldwin, J. E.; Cutting, J., Dupont, W.;Kruse, L.; Silberman, L; Thomas, R C. J. Chem. Soc., Chem. Commun., 1976, 736..
3. Baldwin, J. E. J. Chem. Soc., Chem. Commun, 1976, 734, 738; Baldwin, J. E.; Cutting, J., Dupont, W.; Kruse, L.; Silberman, L; Thomas, R C. J. Chem. Soc., Chem. Commun., 1976, 736..
4. Andrey, O.; Ducry, L., Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron, 1997, 53, 4339; Bedford, S B ; Bell, K E., Fenton, G., Hayes, C. J.; Knight, D W.; Shaw, D. Tetrahedron Lett., 1992, 33, 6511; Kang, S. H.; Lee, S. B. Tetrahedron Lett., 1993, 34, 7579 and references therein.
5. Andrey, O.; Ducry, L., Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron, 1997, 53, 4339; Bedford, S B ; Bell, K E., Fenton, G., Hayes, C. J.; Knight, D W.; Shaw, D. Tetrahedron Lett., 1992, 33, 6511; Kang, S. H.; Lee, S. B. Tetrahedron Lett., 1993, 34, 7579 and references therein.
6. Andrey, O.; Ducry, L., Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron, 1997, 53, 4339; Bedford, S B ; Bell, K E., Fenton, G., Hayes, C. J.; Knight, D W.; Shaw, D. Tetrahedron Lett., 1992, 33, 6511; Kang, S. H.; Lee, S. B. Tetrahedron Lett., 1993, 34, 7579 and references therein.
7. Knight, D W.; Redfern, A. L.; Gilmore, J. Synlett., 1998, 731.
8. Nicolaou, K. C.; Seitz, S P.; Sipio, W. J.; Blount, J. F J. Am. Chem. Soc., 1979, 101, 3884; Lipshutz, B. H.; Gross, T J. Org. Chem., 1995, 60, 3572 and references therein; For a review, see Harring, S. R., Edstrom, E. D; Livinghouse, T. Adv. Heterocycl. Nat. Prod. Synth., 1992, 2, 299.
9. Nicolaou, K. C.; Seitz, S P.; Sipio, W. J.; Blount, J. F J. Am. Chem. Soc., 1979, 101, 3884; Lipshutz, B. H.; Gross, T J. Org. Chem., 1995, 60, 3572 and references therein; For a review, see Harring, S. R., Edstrom, E. D; Livinghouse, T. Adv. Heterocycl. Nat. Prod. Synth., 1992, 2, 299.
10. Nicolaou, K. C.; Seitz, S P.; Sipio, W. J.; Blount, J. F J. Am. Chem. Soc., 1979, 101, 3884; Lipshutz, B. H.; Gross, T J. Org. Chem., 1995, 60, 3572 and references therein; For a review, see Harring, S. R., Edstrom, E. D; Livinghouse, T. Adv. Heterocycl. Nat. Prod. Synth., 1992, 2, 299.
11. Eames, J.; Delasheras, M. A.; Warren, S. Tetrahedron Lett., 1996, 37, 4077 and references therein.
12. Ohsawa, T.; Ihara, M.; Fukumoto, K., Kametani, T. J. Org. Chem., 1983, 48, 3644.
13. Knight, D. W.; Redfern, A. L.; Gilmore, J. Tetrahedron Lett., 1998, 39, 8909.
14. Berthe, B.; Outurquin, F.; Paulmier, C Tetrahedron Lett., 1997, 38, 1393.