Sulfonamides as novel terminators of cationic cyclisations

Chemical Communications

Volumn , Issue 22, 2002, Pages 2724-2725

  Haskins, Charlotte M ^a   Knight, David W ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONAMIDE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CARBOCATION; CATALYST; CHEMICAL PARAMETERS; CHEMICAL REACTION; CYCLIZATION;

EID: 0036435839     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b207755h     Document Type: Article

References (11)

1. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734; J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman and R. C. Thomas, J. Chem. Soc., Chem. Commun., 1976, 736.
2. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734; J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman and R. C. Thomas, J. Chem. Soc., Chem. Commun., 1976, 736.
3. D. W. Knight, Prog. Heterocycl. Chem., 2002, 14, in press.
4. A. D. Jones, D. W. Knight and D. E. Hibbs, J. Chem. Soc., Perkin Trans. 1, 2001, 1182.
5. A. D. Jones, D. W. Knight, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 1999, 40, 3267.
6. G. Stork, A. Y. W. Leong and A. M. Touzin, J. Org. Chem., 1976, 41, 3491.
7. Structural and stereochemical assignments were made by comparisons with authentic compounds, obtained by deiodination of the corresponding iodopyrrolidines whose structures have been determined by extensive NMR studies and confirmed by X-ray crystallography (ref. 3).
8. J. K. Sutherland, Comp. Org. Synth., 1991, 3, 341.
9. For a recent contribution, see: W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gantier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke and K. J. Bancroft, J. Org. Chem., 1999, 64, 9587.
10. Detailed mass spectral analyses of cyclised products 28, 30 and 32 provided excellent additional evidence for these structural assignments. We are grateful to Dr N. J. Haskins for these data which will be published elsewhere.
11. Full analytical and spectroscopic data consistent with the proposed structures have been obtained for all structures reported herein.