3,3′-Br2-BINOL-Zn complex: A highly efficient catalyst for the enantioselective hetero-Diels-Alder reaction

Organic Letters

Volumn 4, Issue 24, 2002, Pages 4349-4352

  Du, Haifeng ^a   Long, Jiang ^a   Hu, Jieyu ^a   Li, Xin ^a   Ding, Kuiling ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013263752     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027034r     Document Type: Article

References (45)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994.
2. (b) Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
3. (c) Kagan, H. B. Comprehensive Organic Chemistry; Pergamon: Oxford, UK, 1992; Vol. 8.
4. (d) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vols. I-III.
5. (e) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: New York, 2001.
6. For reviews see: (a) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15-23.
7. (b) Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558-3588.
8. (c) Maruoka, K. In Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8A.
9. (a) Boger, D. L.; Weinreb, S. N. In Hetero Diels-Alder Methodology in Organic Synthesis; Wasserman, H. H., Ed.; Academic Press: San Diego, CA, 1987.
10. (b) Tietze, L. F.; Kettschau, G. In Stereoselective Heterocyclic Synthesis I; Metz, P., Ed.; Springer; Berlin, Germany, 1997.
11. Danishefsky, S.; Kerwin, J. F.; Kobayashi, S. J. Am. Chem. Soc. 1982, 104, 358-360.
12. (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312.
13. (b) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jorgensen, K. A. Chem. Eur. J. 2000, 6, 123-128.
14. Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910.
15. 8-BINOL-Ti catalyzed asymmetric HDA of Danishefsky's diene with aldehydes in the presence or absence of molecular sieves (MS), see: (a) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820.
16. (b) Keck, G. E.; Li, X. Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998-5999.
17. (c) Wang, B.; Feng, X.; Cui, X.; Liu, H.; Jiang, Y. Chem. Commun. 2000, 1605-1606.
18. (d) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11.
19. (e) Yuan, Y.; Long, J.; Li, X.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042.
20. (f) For BINOL-Zr catalyzed asymmetric HDA of Danishefsky's diene with aldehydes, see: Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. Org. Lett. 2002, 4, 1221-1223.
21. (a) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
22. (b) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398-2400.
23. (c) Li, L.-S.; Wu, Y.; Hu, Y.-J.; Xia, L.-J.; Wu, Y.-L. Tetrahedron: Symmetry 1998, 9, 2271-2277.
24. Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367.
25. (a) Yao, S.; Johennsen, M.; Audrain, H.; Hazell, R. G.; Jorgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599-8605.
26. (b) Jorgensen, K. A.; Johennsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605-613.
27. (c) Dalko, P. I.; Moisan, L.; Cossy, J. Angew. Chem., Int. Ed. 2002, 41, 625-628.
28. (a) Danishefsky, S. J.; Maring, C.; Bednarski, M. Tetrahedron Lett. 1983, 24, 3451-3454.
29. (b) Danishefsky, S. J.; Bednarski, M. J. Am. Chem. Soc. 1983, 105, 6968-6969.
30. (a) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79-80.
31. (b) Qian, C.; Wang, L. Tetrahedron Lett. 2000, 41, 2203-2206.
32. (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004.
33. (b) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497-2500.
34. (c) Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861-863.
35. (d) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367-3368.
36. (a) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466-2467.
37. (b) Kumagai, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2001, 3, 4251-4254.
38. Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1985, 26, 5536-5538.
39. Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735-1738.
40. For comprehensive reviews on NLE in asymmetric catalysis, see: (a) Fenwick, D. R.; Kagan H. B. In Topics in Stereochemistry; Denmark, S. E., Ed.; John Wiley & Sons: New York, 1999; Vol. 22, pp 257-296.
41. (b) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2959.
42. (c) Bolm, C. In Advanced Asymmetric Catalysis; Stephenson, G. R., Ed.; Chapman & Hall: London, UK, 1996; pp 9-26.
43. (d) Heller, D.; Drexler, H.-J.; Fischer, C.; Buschmann, H.; Baumann, W.; Heller, B. Angew. Chem., Int. Ed. 2000, 39, 495-499.
44. (e) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832-4842.
45. (f) Blackmond, D. G. J. Am. Chem. Soc. 1998, 120, 13349-13353.