Stereoselective synthesis of substituted tetrahydrofurans using 5-Endo- trig cyclisation reactions

Tetrahedron

Volumn 55, Issue 47, 1999, Pages 13471-13494

  Craig, Donald ^a   Ikin, Neil J ^a   Mathews, Neil ^b   Smith, Alison M ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b WELLCOME RESEARCH LABORATORIES   (United Kingdom)

Author keywords

Cyclisation; Sulfone; Synthesis; Tetrahydrofuran

Indexed keywords

ALCOHOL DERIVATIVE; SULFONE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033585128     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00832-7     Document Type: Article

References (20)

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2. (ii) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754.
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4. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738. For some recent examples of the use of 5-endo-trig reactions in heterocycle synthesis, see: Minamikawa, J.; Nishi, T. Bioorg. Med. Chem. Lett. 1997, 7, 1267-1268; Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339-4352; Jones, A. D.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1996, 915-916.
5. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738. For some recent examples of the use of 5-endo-trig reactions in heterocycle synthesis, see: Minamikawa, J.; Nishi, T. Bioorg. Med. Chem. Lett. 1997, 7, 1267-1268; Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339-4352; Jones, A. D.; Knight, D. W. J. Chem.Soc., Chem. Commun. 1996, 915-916.
6. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738. For some recent examples of the use of 5-endo-trig reactions in heterocycle synthesis, see: Minamikawa, J.; Nishi, T. Bioorg. Med. Chem. Lett. 1997, 7, 1267-1268; Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339-4352; Jones, A. D.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1996, 915-916.
7. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738. For some recent examples of the use of 5-endo-trig reactions in heterocycle synthesis, see: Minamikawa, J.; Nishi, T. Bioorg. Med. Chem. Lett. 1997, 7, 1267-1268; Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339-4352; Jones, A. D.; Knight, D. W. J. Chem.Soc., Chem. Commun. 1996, 915-916.
8. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738. For some recent examples of the use of 5-endo-trig reactions in heterocycle synthesis, see: Minamikawa, J.; Nishi, T. Bioorg. Med. Chem. Lett. 1997, 7, 1267-1268; Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339-4352; Jones, A. D.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1996, 915-916.
9. Preliminary communications: (i) Craig, D.; Smith, A. M. Tetrahedron Lett. 1992, 33, 695-698;
10. (ii) Craig, D.; Ikin, N. J.; Mathews, N.; Smith, A. M. Tetrahedron Lett. 1995, 36, 7531-7534.
11. Julia, M.; Launay, M.; Stacino, J.-P.; Verpeaux, J.-N. Tetrahedron Lett. 1982, 23, 2465-2468.
12. The threo-selectivity may be rationalised using the Cram or Felkin-Anh models, treating the sulfonyl group as the largest α-substituent.
13. 2 = Me.
14. We thank Mr Dick Sheppard and Mr Paul Hammerton of this Department for these determinations.
15. We presume that the unusually low temperature at which the syn-elimination took place stems from relief of steric crowding in the putative intermediate sulfoxide.
16. Jones and Liotta have reported that on the basis of MNDO calculations phenylthio-substituted cyclic oxonium ions derived from pyrans are viable alternatives to the postulated episulfonium species in the substitution-rearrangement reactions of some phenylthiopyranosides. See: Jones, D. K.; Liotta, D. C. Tetrahedron Lett. 1993, 34, 7209-7212.
17. Craig, D.; Lawrence, R. M.; Tapolczay, D. J. Synlett 1997, 1001-1003.
18. Berry, M. B.; Craig, D.; Jones, P. S.; Rowlands, G. J. Chem. Commun. 1997, 2141-2142; Craig, D.;Jones, P. S.; Rowlands, G. J. Synlett 1997, 1423-1425.
19. Berry, M. B.; Craig, D.; Jones, P. S.; Rowlands, G. J. Chem. Commun. 1997, 2141-2142; Craig, D.; Jones, P. S.; Rowlands, G. J. Synlett 1997, 1423-1425.
20. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd Edn.; Pergamon: Oxford, 1988.