Intramolecular oxygen radical additions to α,β-unsaturated esters. Diastereoselective tandem cyclofunctionalization and hydrogen transfer reactions

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 339-342

  Guindon, Yvan ^a   Denis, Réal C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

OXY;

EID: 0032576803     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10515-9     Document Type: Article

References (47)

1. 1. For reviews, see: (a) Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296-304.
2. (b) Smadja, W. Synlett 1994, 1-26.
3. (c) Curran, D.P.; Porter, N.A.; Giese, B. Stereochemistry of Radical Reactions - Concepts, Guidelines and Synthetic Applications, VCH, New York, 1995.
4. 2. Examples of substrate control: (a) Hart, D.J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470.
5. (b) Giese, B.; Damm, W.; Wetterich, F.; Zeitz, H.-G. Tetrahedron Lett. 1992, 33, 1863-1866.
6. (c) Giese, B.; Damm, W.; Wetterich, F.; Zeitz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885-5888.
7. (d) Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841-4858.
8. (e) Porter, N.A.; Carter, R.L.; Mero, C.L.; Roepel, M.G.; Curran, D.P. Tetrahedron 1996, 52, 4181-4198.
9. (f) Sibi, M.P.; Ji, J.G. J. Am. Chem. Soc. 1996, 118, 3063-3064.
10. (g) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508.
11. 3. Examples of reagent control: (a) Wu, J.H.; Radinov, R.; Porter, N.A. J. Am. Chem. Soc. 1995, 117, 11029-11030.
12. (b) Sibi, M.P.; Jasperse, C.P.; Ji, J.G. J. Am. Chem. Soc. 1995, 117, 10779-10780.
13. (c) Fhal, A.R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661-2664.
14. 4. (a) Guindon, Y.; Yoakim, C.; Lemieux, R.; Boisvert, L.; Delorme, D.; Lavallée, J.-F. Tetrahedron Lett. 1990, 31, 2845-2848.
15. (b) Guindon, Y.; Lavallée, J.-F.; Boisvert, L.; Chabot, C.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R.; Simoneau, B. Tetrahedron Lett. 1991, 32, 27-30.
16. (c) Durkin, K.; Liotta, D.; Rancourt, J.; Lavallée, J.-F.; Boisvert, L.; Guindon, Y. J. Am. Chem. Soc. 1992, 114, 4912-4914.
17. (d) Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W.W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J.; Durkin, K.; Liotta, D. J. Org. Chem. 1994, 59, 1166-1178.
18. 5. (a) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702.
19. (b) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett. 1995, 449-451.
20. (c) Guindon, Y.; Guérin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Pure & Appl. Chem. 1996, 68, 89-96.
21. (d) Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, in press.
22. 6. Examples of the use of Lewis acids in substrate control: (a) Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803-7805.
23. (b) Renaud, P.; Moufid, N.; Kuo, L.H.; Curran, D.P. J. Org. Chem. 1994, 59, 3547-3552.
24. 7. (a) Clerici, A.; Porta, O. J. Chem. Soc. Perkin Trans II 1980, 1234-1237.
25. (b) Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1988, 110, 4415-4416.
26. (c) Beckwith, A.L.J.; Hay, B.P.; Williams, G.M. J. Chem. Soc. Chem. Commun. 1989, 1202-1203.
27. (d) Gallou, F.; Hartung, J. J. Org. Chem. 1995, 60, 6706-6716.
28. (e) Hartung, J. Liebigs Annals 1996, 9, 1425-1436.
29. (f) Hartung, J.; Storm, R.; Witt, D.; Bringman G. Ange. Chim. Int. Ed. 1997, 35, 2820-2823.
30. (g) Allyloxy radical: Johns, A.; Murphy, J.A. Tetrahedron Lett. 1988, 837-840.
31. (h) Alkenyloxycarbonyloxy radical: Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett. 1991, 32, 45-48.
32. (i) Beckwith, A.L.J.; David, I.G.E. Tetrahedron Lett. 1991, 49-52.
33. 8. (a) Reference lc.
34. (b) Babu R. Acc. Chem. Res. 1991, 24, 139-145.
35. (c) Jaspere, C.P.; Curran, D.P.; Fevig, T.L. Chem. Rev. 1991, 91, 1237-1286.
36. (d) Hart, D.J. Science 1984, 223, 883-887.
37. 9. Ingold, K.O. in Free Radicals; Kochi, J.K. Ed.; John Wiley and Sons: New York, 1973, pp 37-112.
38. 10. McDougal, P.G.; Rico, J.G.; Oh, Y.-I.; Condon, B.D. J. Org. Chem. 1986, 51, 3388-3390.
39. 11. Yields were determined by recovery of isolated products and by NMR measurement using benzyl alcohol as internal standard. The discrepancy between isolated and NMR yields is due to product volatility and consequent losses during concentration under reduced pressure.
40. 12. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, É.; Jung, G. J. Org. Chem. 1995, 60, 288-289.
41. 13. (a) Beckwith, A.L.J.; Easton, C.J.; Lawrence, T.; Serelis, A.K. Aust. J. Chem. 1983, 36, 545-556.
42. (b) Beckwith, A.L.J.; Easton, C.J.; Serelis, A.K. J. Chem. Soc., Chem. Commun. 1980, 482-483.
43. (c) Beckwith, A.L.J.; Lawrence, T.; Serelis, A.K. J. Chem. Soc., Chem. Commun. 1980, 484-485.
44. (d) Beckwith, A.L.J.; Schiesser, C.H. Tetrahedron Lett. 1985, 26, 373-376.
45. (e) Spellmeyer, D.C.; Houk, K.N. J. Org. Chem. 1987, 52, 959-974.
46. 14. For a review on allylic 1,3-strain, see Hoffman, R.W. Chem. Rev. 1989, 89, 1841-1860.
47. 15. The discrepancy in anti/syn ratios between hydrogen transfers of tetrahydropyranyl radicals arising through the fragmentation of benzenesulfenates and those arising from tertiary iodides (ref. 12) may be due to the contribution of a minor ionic pathway in the tandem sequence.