Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans

Tetrahedron

Volumn 53, Issue 12, 1997, Pages 4339-4352

  Andrey, Olivier ^a   Ducry, Laurent ^a   Landais, Yannick ^a   Planchenault, Denis ^a   Weber, Valéry ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031585115     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00109-9     Document Type: Article

References (55)

1. 1. Baldwin, J.E. J. Chem. Soc., Chem. Commun., 1976, 734-736.
2. 2. (a) Bedford, S.B.; Fenton, G.; Knight, D.W.; Shaw, D. Tetrahedron Lett., 1992, 33, 6505-6506;
3. (b) Bennett, F.; Bedford, S.B.; Bell, K.E.; Fenton, G.; Knight, D.W.; Shaw, D. Tetrahedron Lett., 1992, 33, 6507-6510;
4. (c) Bedford, S.B.; Bell, K.E.; Fenton, G.; Hayes, C.J; Knight, D.W.; Shaw, D. Tetrahedron Lett., 1992, 33, 6511-6514;
5. (d) Kang, S.H.; Hwang, T.S.; Kim, W.J.; Lim, J.K. Tetrahedron Lett., 1990, 31, 5917-5920;
6. (e) Knight, D.W.; Shaw, D.; Fenton, G. Synlett, 1994, 295-296;
7. (f) Barks, J.M.; Knight, D.W.; Seaman, C.J.; Weingarten, G.G. Tetrahedron Lett., 1994, 35, 7259-7262;
8. (g) Barks, J.M.; Knight, D.W.; Weingarten, G.G. J. Chem. Soc., Chem. Commun., 1994, 719-720;
9. (h) Kang, S.H.; Hwang, T.S.; Kim, W.J.; Lim, J.K. Tetrahedron Lett., 1990, 31, 5917-5920;
10. (i) Kang, S.H.; Lee, S.B. Tetrahedron Lett., 1993, 34, 1955-1958;
11. (j) Kang, S.H.; Lee, S.B. Tetrahedron Lett., 1993, 34, 7579-7582;
12. (k) Lipshutz, B.H.; Barton, J.C. J. Am. Chem. Soc., 1992, 114, 1084-1086;
13. (l) Lipshutz, B.H.; Tirado, R. J. Org. Chem., 1994, 59, 8307-8311;
14. (m) Mihelich, E.D.; Hite, G.A. J. Am. Chem. Soc., 1992, 114, 7318-7319;
15. (n) Evans, R.D.; Magee, J.W.; Schauble, J.H. Synthesis, 1988, 862-868;
16. (o) Galatsis, P.; Parks, D.J. Tetrahedron Lett., 1994, 35, 6611-6614;
17. (p) Galatsis, P.; Millan, S.D.; Nechala, P.; Ferguson, G. J. Org. Chem., 1994, 59, 6643-6651;
18. (q) Galatsis, P.; Manwell, J.J. Tetrahedron Lett., 1995, 36, 8179-8182.
19. 3. Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915-916.
20. 4. (a) Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1994, 35, 9549-9552;
21. (b) Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. J. Org. Chem., (In print).
22. 5. For a preliminary communication, see : Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1995, 36, 2987-2990.
23. 6. For reviews on the use of the silicon group as a masked hydroxy group, see : (a) Fleming, I. Chemtracts, Org. Chem., 1996, 9, 1-64;
24. (b) Jones, G.R.; Landais, Y. Tetrahedron, 1996, 52, 7599-7662.
25. 7. Landais, Y.; Planchenault, D. Synlett, 1995, 1191-1193.
26. 8. For studies about kinetic vs thermodynamic control of related reactions, see: (a) Harding, K.E.; Marman, T.H. J. Org. Chem., 1984, 49, 2838-2840;
27. (b) Harding, K.E.; Marman, T.H.; Nam, D. Tetrahedron Lett., 1988, 29, 1627-1630;
28. (c) Bartlett, P.A.; Myerson, J. J. Am. Chem. Soc., 1978, 100, 3950-3952.
29. 9. Fleming, I.; Dunoguès, J.; Smithers, R. Org. React., 1989, 37, 57-575.
30. 10. Hoffmann, R.W. Chem. Rev., 1989, 89, 1841-1860.
31. 11. Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis, Pergamon Press: Oxford, 1986. We gratefully acknowledge one of the referee for suggesting this explanation to us.
32. 12. Streitwieser, A., Jr. Solvolytic Displacement Reactions, Mc Graw Hill : New-York, 1962, 43.
33. 13. Kahn, S.D.; Pau, C.F.; Chamberlin, A.R.; Hehre, W.J. J. Am. Chem. Soc., 1987, 109, 650-663 and references cited therein.
34. 14. (a) White, J.M. Aust. J. Chem., 1995, 48, 1227-1251;
35. (b) Lambert, J.B. Tetrahedron, 1990, 46, 2677-2689.
36. 15. The fact that steric and electronic effects are co-operative during most electrophilic reactions on allylsilanes have made difficult the evaluation of the origin of the stereocontrol during these reactions. See : Fleming, I.; Jones, G.R.; Kindon, N.D.; Landais, Y.; Leslie, C.P.; Morgan, I.T.; Peukert, S.; Sarkar, A.K. J. Chem. Soc., Perkin Trans. 1, 1996, 1171-1196 and references cited therein.
37. 16. Calculations are now under way in our laboratory to rationalize this reversal of the diastereocontrol.
38. 17. (a) Andrey, O.; Landais, Y. Tetrahedron Lett., 1993, 34, 8435-8438;
39. (b) Fleming, I. Pure & Appl. Chem., 1988, 60, 71-78;
40. (c) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron, 1996, (In print).
41. 18. (a) Servens, C.; Pereyre, M. J. Organomet. Chem., 1971, 26, C4-C6;
42. (b) Grignon, J.; Pereyre, M. J. Organomet. Chem., 1973, 61, C33-C35;
43. (c) Grignon, J.; Servens, C.; Pereyre, M. J. Organomet. Chem., 1975, 96, 225-235;
44. (d) Keck, G.; Enholm, E.J.; Yates, J.B.; Wiley, M.R. Tetrahedron, 1985, 41, 4079-4094;
45. (e) Landais, Y.; Planchenault, D. Tetrahedron, 1995, 51, 12097-12108.
46. 19. Fleming, I.; Henning, R.; Parker, D.C.; Plaut, H.E.; Sanderson, P.E.J. J. Chem. Soc., Perkin Trans 1, 1995, 317-337.
47. 20. (2-Furyl)silyl group has been used previously but was found to be less stable than the thienyl analogue, see: (a) Stork, G. Pure & Appl. Chem., 1989, 61, 439-442;
48. (b) Norley, M.C.; Kocienski, P.J.; Faller, A. Synlett, 1994, 77-78.
49. 21. For a recent discussion concerning the formation of vinylsilanes during hydrosilylation of olefins, see : Brown, J.M.; Lloyd-Jones, G.C. J. Am. Chem. Soc., 1994, 116, 866-878 and references cited therein.
50. 22. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics, 1983, 2, 1694-1696
51. 23. For the use of allylsilyl groups as masked hydroxy group, see : (a) Tamao, K.; Ishida, N. Tetrahedron Lett., 1984, 25, 4249-4252;
52. (b) Magar, S.S.; Fuchs, P.L. Tetrahedron Lett., 1991, 32, 7513-7516;
53. (c) Magar, S.S.; Desai, R.C.; Fuchs, P.L. J. Org. Chem., 1992, 57, 5360-5369;
54. (d) Fleming, I.; Winter, S.B.D. Tetrahedron Lett., 1993, 34, 7287-7290;
55. (e) Fleming, I.; Winter, S.B.D. Tetrahedron Lett., 1995, 36, 1733-1734.