Synthesis of 2,5-disubstituted 3-(phenylsulfonyl)pyrrolidines via 5-endo-trig cyclisation reactions

Synlett

Volumn , Issue 12, 1997, Pages 1423-1425

  Craig, Donald ^a   Jones, Philip S ^b   Rowlands, Gareth J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002990696     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1054     Document Type: Article

References (21)

1. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736.
2. For examples of 5-endo-trig reactions giving rise to pyrrolidines, see: Padwa, A.; Norman, B. H. J. Org. Chem. 1990, 55, 4801-4807.
3. For a recent report describing iodonium ion-mediated cyclisations which give pyrrolidines via overall 5-endo-trig cyclisation processes, see: Jones, A. D.; Knight, D. W. Chem. Commun. 1996, 915-916.
4. Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: Oxford, 1993.
5. Craig, D.; Smith, A. M. Tetrahedron Lett. 1992, 33, 695-698;
6. Craig, D.; Ikin, N. J.; Mathews, N.; Smith, A. M. Tetrahedron Lett. 1995, 36, 7531-7534.
7. For the work which inspired our initial investigations, see: Knochel, P.; Normant, J. F. Tetrahedron Lett. 1985, 26, 4455-4458.
8. 13C nmr and ir spectra, and which showed low-resolution ms and either elemental combustion analysis or high-resolution ms characteristics in accord with the assigned structures.
9. (i) Osborn, H. M. I.; Sweeney, J. B.; Howson, W. Synlett 1994, 145-147;
10. (ii) Osborn, H. M. I.; Cantrill, A. A.; Sweeney, J. B.; Howson, W. Tetrahedron Lett. 1994, 35, 3159-3162.
11. All attempts to effect reaction of the dianions of 4 with aldehydes met with failure. The dianions generated from the N-tosyl analogues of 4 reacted efficiently with aldehydes.
12. Julia, M.; Launay, M. Stacino, J.; Verpeaux, J. Tetrahedron Lett. 1982, 23, 2465-2468.
13. Berry, M. B., Ph.D. thesis, University of London, 1993.
14. Julia, M.; Stacino, J. Tetrahedron 1986, 42, 2469-2474;
15. Cuvigny, T.; du Penhoat, C. H.; Julia, M. Tetrahedron 1986, 42, 5329-5336.
16. Treatment of 6a-f with potassium tert-butoxide-THF gave mixtures of pyrrolidines 7 and vinylic sulfones E-8 in low yields.
17. We thank Mr Dick Sheppard and Mr Paul Hammerton of this department for these determinations.
18. o|), 2θ<124°] and 356 parameters. The absolute polarity was determined by use of the Flack parameter which refined to a value of lengths and angles, and thermal parameters for 7c and 7g have been deposited at the Cambridge Crystallographic Data Centre.
19. Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. J. Chem. Soc., Perkin Trans. 1 1985, 1217-1226, and references therein.
20. Künzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1991, 32, 1949-1952.
21. 3PS requires C, 70.32; H, 6.23; N, 2.65%).