Diastereocontrol in the intramolecular cycloadditions of 2- substituted-erythro-3,4-isopropylidenedioxyhex-5-enenitrile oxides

Tetrahedron

Volumn 55, Issue 52, 1999, Pages 15167-15180

  Gallos, John K ^a   Koumbis, Alexandros E ^a   Xiraphaki, Vassiliki P ^a   Dellios, Constantinos C ^a   Coutouli Argyropoulou, Evdoxia ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Carbohydrates; Cycloadditions; Diastereoselection; Isoxazolines; Nitrile oxides

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; CARBOHYDRATE DERIVATIVE; ISOXAZOLINE DERIVATIVE; NITRILE; OXIDE; SUGAR ALCOHOL;

ARTICLE; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033601415     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00991-6     Document Type: Article

References (51)

1. (a) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779 and references cited there.
2. (b) Knapp, S. Chem. Soc. Rev. 1999, 28, 61 and references cited there.
3. (c) Kobayashi, Y. Carbohydr. Res. 1999, 315, 3.
4. (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
5. (b) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
6. (c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
7. (a) Gallos, J. K.; Goga, E. G.; Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613.
8. (b) Marco-Contelles, J.; Rodríguez-Fernández, Ma. M. Tetrahedron: Asymmetry 1997, 8, 2249.
9. D value is that reported by Marco-Contelles and coworkers in ref. 3b.
10. (a) Gallos, J. K.; Koumbis, A. E.; Apostolakis, N. E. J. Chem. Soc., Perkin Trans. 1 1997, 2457.
11. (b) Gallos, J. K.; Koftis, T. V.; Karamitrou, V. I.; Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1997, 2461.
12. (c) Gallos, J. K.; Koftis, T. V.; Koumbis, A. E.; Moutsos, V. I. Synlett 1999, 1289.
13. (a) Padwa, A., Ed.; 1,3-dipolar Cycloaddition Chemistry; Wiley-Interscience: New York, 1984.
14. (b) Curran, D. P. Adv. Cycloaddition 1988, 1, 129.
15. (c) Torsell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1989.
16. (d) Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410.
17. (e) Jäger, V.; Grund, H.; Buß, V.; Schwab, W.; Müller, I.; Schohe, R.; Franz, R.; Ehrler, R. Bull. Soc. Chim. Belg. 1983, 92, 1039.
18. (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
19. (b) Tatsuta, K.; Niwata, Y.; Umezawa, K.; Toshima, K.; Nakata, M. Tetrahedron Lett. 1990, 31, 1171.
20. (c) Duclos, O.; Mondange, M.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1992, 33, 8061.
21. (d) Takahashi, T.; Nakazawa, M.; Sakamoto, Y.; Houk, K. N. Tetrahedron Lett. 1993, 34, 4075.
22. (e) Lygo, B.; Swiatyj, M.; Trabsa, H.; Voyle, M. Tetrahedron Lett. 1994, 35, 4197.
23. (f) Tatsuta, K.; Niwata, Y.; Umezawa, K.; Toshima, K.; Nakata, M. Carbohydr. Res. 1991, 222, 189.
24. Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363.
25. (a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065.
26. (b) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813.
27. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990.
28. Moutel, S.; Shipman, M. Synlett 1998, 1333.
29. Arnone, A.; Cavcchioli, M.; Donadelli, A.; Resnati, G. Tetrahedron: Asymmetry 1994, 5, 1019.
30. (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
31. (b) Dehaen, W.; Hassner, A. Tetrahedron Lett. 1990, 31, 743.
32. (c) Kim, H. R.; Kim, H. J.; Duffy, J. L.; Olmstead, M. M.; Ruhlandt-Senge, K.; Kurth, M. J. Tetrahedron Lett. 1991, 32, 4259.
33. (d) Brown, F. K.; Raimondi, L.; Wu, Y.-D.; Houk K. N. Tetrahedron Lett. 1992, 33, 4405.
34. (e) Jung M. E.; Vu, B. T. Tetrahedron Lett. 1996, 37, 451.
35. (f) Jung M. E.; Vu, B. T. J. Org. Chem. 1996, 61, 4427.
36. (g) Liu, J.-T.; Lin, W.-W.; Jang, J.-J.; Liu, J.-Y.; Yan, M.-C.; Hung, C.; Kao, K.-H.; Wang, Y.; Yao, C.-F. Tetrahedron, 1999, 55, 7115.
37. (h) Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M.; Hassner, A.; Murthy, K. S. K.; Tetrahedron Lett. 1988, 29, 4169.
38. (j) Hassner, A.; Dehaen, W. J. Org. Chem. 1990, 55, 5505.
39. (a) Lee, G. A. Synthesis 1982, 508.
40. (b) Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
41. Kaskar, B.; Heise, G. L.; Michalak, R. S.; Vishnuvajjala, B. R. Synthesis 1990, 1031.
42. Webb, T. H.; Thomasco, L. M.; Schlachter, S. T.; Gaudino, J. J.; Wilcox, C. S. Tetrahedron Lett. 1988, 29, 6823.
43. nd Ed., Wiley-Interscience: New York, 1991.
44. (b) Kocienski, P. J. Protecting Groups, Georg Thieme Verlag: Stuttgart, 1994.
45. (a) Knight, J.; Parsons, P. J. J. Chem. Soc., Chem. Commun. 1987, 189.
46. (b) Knight, J.; Parsons, P. J. J. Chem. Soc., Perkin Trans. 1. 1989, 979.
47. (a) Andruszkiewicz, R.; Silverman, R. B. Synthesis 1989, 953.
48. (b) Patrocinio, V. L., Costa, P. R. R.; Correia, C. R. D. Synthesis 1994, 474.
49. (c) Costa, J. S.; Dias, A. G.; Anholeto, A. L.; Monteiro, M. D.; Patrocinio, V. L., Costa, P. R. R. J. Org. Chem. 1997, 62, 4002.
50. Young, D. G. J.; Gomez-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692.
51. Kozikowski, A. P.; Chen, Y. Y. Tetrahedron Lett. 1982, 23, 2081.