Use of bis(oxazoline)-metal complexes as chiral catalysts for asymmetric Diels-Alder reactions using 2-acetyl-1,4-naphthoquinone as a dienophile

Tetrahedron Asymmetry

Volumn 8, Issue 24, 1997, Pages 4069-4078

  Brimble, Margaret A ^a   McEwan, John F ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584575     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00562-4     Document Type: Article

References (35)

1. For reviews see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis, 1990, Pergamon Press,
2. (b) Giuliano, R. M. Cycloaddition Reactions in Carbohydrate Chemistry, 1992, American Chemical Society, Washington DC and references cited therein
3. For reviews see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes, Doyle, M. P., Ed., JAI Press, Greenwich, CT, 1995, vol. 1, pp. 29-59.
4. (b) Kagan, H. B.; Riant, O. Chem. Rev., 1992, 92, 1007.
5. Narasaka, K. Synthesis, 1991, 1.
6. For an example see: Coxon, J. M.; MacLagan, R. G. A. R.; McDonald, Q.; Steel, P. J. J. Org. Chem., 1991, 56, 2542.
7. Finley, K. T. In The Chemistry of Quinonoid Compounds, Vol. 2, Part 2, Patai, S.; Rappoport, Z. Eds., Wiley-Interscience, New York, 1988, p. 537.
8. (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc., 1980, 102, 7595.
9. (b) Larsen, D. S.; Stoodley, R. J. Tetrahedron, 1990, 46, 4711.
10. Maruoka, K.; Sakurai, M.; Fujiwara, J.; Yamamoto, H. Tetrahedron Lett., 1986, 27, 4895.
11. Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc., 1986, 108, 3510.
12. Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem., 1994, 59, 1179.
13. Mikami, K.; Motoyama, Y; Terada, M. J. Am. Chem. Soc., 1994, 116, 2812.
14. For related fragmentations see: Brimble, M. A.; Elliott, R. J. Tetrahedron, 1997, 53, 7715 and references cited therein.
15. Kaufmann; Boese, R. Angew. Chem. Int. Ed. Engl., 1990, 29, 545.
16. Kobayashi, K.; Ishitani, H. J. Am. Chem. Soc., 1994, 116, 4083.
17. Takemura, H.; Komeshima, N.; Takahashi, I.; Hashimoto, S.; Ikota, N.; Tomioka, K.; Koga, K. Tetrahedron Lett., 1987, 28, 5687.
18. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc., 1986, 108, 7060.
19. (a) Corey, E. J.; Ishihara, K. Tetrahedron Lett., 1992, 33, 6807.
20. (b) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc., 1991, 113, 728.
21. (a) Evans, D. A.; Lectka, T.; Miller, S. Tetrahedron Lett., 1993, 34, 7027.
22. (b) Evans, D. A.; Miller, S.; Lectka, T. J. Am. Chem. Soc., 1993, 115, 6460.
23. (c) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl., 1995, 34, 798.
24. (d) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett., 1996, 37, 7481
25. (e) Evans, D. A.; Johnson, J. S. J. Org. Chem., 1997, 62, 786.
26. (a) Desimoni, G.; Faita, G.; Righetti, P. P. Tetrahedron Lett., 1996, 37, 3027.
27. (b) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron, 1997, 53, 7671.
28. (a) Takacs, J. M.; Lawson, E. C.; Reno, M. J.; Youngman, M. A.; Quincy, D. A. Tetrahedron; Asymmetry, 1997, 8, 3073.
29. (b) Takacs, J. M.; Quincy, D. A.; Shay, W; Jones, B. E.; Ross, C. R. Tetrahedron; Asymmetry, 1997, 8, 3079 .
30. (a) Johannsen, M.; Jorgensen, K. A.; J. Org. Chem., 1995, 60, 5757.
31. (b) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron; Asymmetry, 1996, 7, 2165.
32. Chorn, T. A.; Giles, R. G. F.; Green, I. R.; Hugo, V. I.; Mitchell, P. R. K.; Yorke, S. C. J Chem. Soc., Perkin Trans 1, 1984, 1339.
33. Uno, H. J Org. Chem., 1986, 51, 350.
34. Ichihara, A.; Ubukata, M.; Sakamura, S., Agric. Biol. Chem., 1980, 44, 211.
35. Brimble, M. A.; Stuart, S. J. J. Chem. Soc., Perkin Trans. 1, 1990, 881.