Isopropylidene acetals: Tether control groups for asymmetric intramolecular Diels-Alder reactions

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 7045-7048

  Wong, Timothy ^a   Wilson, Peter D ^a   Woo, Simon ^a   Fallis, Alex G ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE;

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

BETULACEAE;

EID: 0030824519     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01708-5     Document Type: Article

References (46)

1. (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
2. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I.; Paquette, L.A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 315, Weinreb, S.M., op. cit., p 401; Boyes, D.L., op. cit., p 451; Roush, W.R., op. cit., p 513.
3. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I.; Paquette, L.A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 315, Weinreb, S.M., op. cit., p 401; Boyes, D.L., op. cit., p 451; Roush, W.R., op. cit., p 513.
4. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I.; Paquette, L.A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 315, Weinreb, S.M., op. cit., p 401; Boyes, D.L., op. cit., p 451; Roush, W.R., op. cit., p 513.
5. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I.; Paquette, L.A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 315, Weinreb, S.M., op. cit., p 401; Boyes, D.L., op. cit., p 451; Roush, W.R., op. cit., p 513.
6. (a) Fallis, A. G. Can. J. Chem. 1984, 62, 183.
7. (b) Ciganek, E. Org. React. 1984, 32, 1.
8. (c) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
9. Hirama, M.; Uei, M. J. Am. Chem. Soc. 1982, 104, 4251.
10. Millan, S.; Pham, T.; Lavers, J.; Fallis, A. G. Tetrahedron Lett. 1997, 38, 795.
11. (a) Taznao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 6478.
12. (b) Shea, K. J.; Zandi, K. S.; Staab, A. J.; Carr, R. Tetrahedron Lett. 1990, 31, 5885.
13. (c) Craig, D.; Reader, J. C. Tetrahedron Lett. 1990, 31, 6586.
14. (d) Gillard, J.W.; Fortin, R.; Grimm, E. L.; Maillard, M.; Tjepkema, M.; Bernstein, M. A.; Glaser, R. Tetrahedron Lett. 1991, 32, 1145.
15. (e) Stork, G.; Chan, T. Y.; Breault, G. J. Am. Chem. Soc. 1992, 114, 7578.
16. Craig, D; Reader, J. C. Tetrahedron Lett. 1992, 33, 6165.
17. Craig, D.; Ford, M. J.; Stones, J. A. Tetrahedron Lett. 1996, 37, 535.
18. (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
19. (b) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
20. (c) Pinder, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741.
21. (d) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611.
22. (e) Seebach, D.; Dahinder, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnk, F. N. M. J. Org. Chem. 1995, 60, 1788.
23. (f) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 398.
24. (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. Tetrahedron Lett. 1984, 25, 4071.
25. (b) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261.
26. (c) Alsono, I.; Carretero, J. C.; Garcia Ruano, J. L. J. Org. Chem. 1994, 59, 1499.
27. (d) Oppolzer, W.; Seletsky, B. M.; Bernardinelli, G. Tetrahedron Lett. 1994, 35, 3509.
28. Stork, G.; Chan, T. Y, J. Am. Chem. Soc. 1995, 117, 6595.
29. Evans, D. A. ; Johnson, J. S. J. Org. Chem. 1997, 62, 786.
30. Marco-Contelles, J.; Destabel, C.; Callego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1996, 61, 1354.
31. Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 12336.
32. Coe, J. W.; Roush, W. R. J. Org. Chem. 1989, 54, 915.
33. Roush, W. R.; Koyama, K.; Curtin, M. L.; Moriarty, K. J. J. Am. Chem. Soc. 1996, 118, 7502.
34. Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337.
35. (a) Wong, T.; Romero, M. A.; Fallis, A. G. J. Org. Chem. 1994, 59, 5527.
36. (b) Wong, T.; Tjepkema, M. W.; Audrain, H.; Wilson, P. D.; Fallis, A. G. Tetrahedron Lett. 1996, 37, 755.
37. Ballou, C. E. J. Am. Chem. Soc. 1957, 79, 165.
38. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkileni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598.
39. X-ray data and figure will be reported in a full paper.
40. π-Facial Diastereoselection in Diels-Alder Cycloadditions and Related Reactions; Fallis, A. G.; Lu, Y.-F., in Adv. in Cycloadditions; Ed. Curran, D.P.; JAI Press: Greenwich, Conn, 1993; Vol. 3, pp 1.
41. (a) Lu, Y.-F.; Fallis, A. G. Tetrahedron Lett. 1993, 45, 3367.
42. (b) Lu, Y.-F.; Fallis, A. G. Can. J. Chem. 1995, 73, 2239.
43. (c) Tjepkema, M. W.; Wilson, P. D.; Wong, T.; Romero, M. A.; Audrain, H.; Fallis, A. G. Tetrahedron Lett. 1995, 36, 6039.
44. (d) Fallis, A. G. Pure Appl. Chem. 1997, 69, 495.
45. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, in press.
46. (f) Tjepkema, M. W.; Wong, T.; Wilson, P. D.; Fallis, A. G. Can. J. Chem. 1997, 75, in press.