Enantioselective catalysis of hetero Diels-Alder reaction and diethylzinc addition using a single catalyst

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1091-1093

  Du, Haifeng ^a   Ding, Kuiling ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ZINC DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; DIELS ALDER REACTION; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 0042998218     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034143c     Document Type: Article

References (27)

1. For leading examples of tandem catalysis, see: (a) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (b) Bielawski, C. W.; Louie, J. R.; Grubbs, H. J. Am. Chem. Soc. 2000, 122, 12872. (c) Drouin, S. D.; Zamanian, F.; Fogg, D. E. Organometallics 2001, 20, 5495. (d) Orita, A.; Nagano, Y.; Nakazawa, K.; Otera, J. Adv. Synth. Catal. 2002, 344, 548. (e) Chen, J.; Otera, J. Angew. Chem., Int. Ed. 1998, 37, 91.
2. For leading examples of tandem catalysis, see: (a) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (b) Bielawski, C. W.; Louie, J. R.; Grubbs, H. J. Am. Chem. Soc. 2000, 122, 12872. (c) Drouin, S. D.; Zamanian, F.; Fogg, D. E. Organometallics 2001, 20, 5495. (d) Orita, A.; Nagano, Y.; Nakazawa, K.; Otera, J. Adv. Synth. Catal. 2002, 344, 548. (e) Chen, J.; Otera, J. Angew. Chem., Int. Ed. 1998, 37, 91.
3. For leading examples of tandem catalysis, see: (a) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (b) Bielawski, C. W.; Louie, J. R.; Grubbs, H. J. Am. Chem. Soc. 2000, 122, 12872. (c) Drouin, S. D.; Zamanian, F.; Fogg, D. E. Organometallics 2001, 20, 5495. (d) Orita, A.; Nagano, Y.; Nakazawa, K.; Otera, J. Adv. Synth. Catal. 2002, 344, 548. (e) Chen, J.; Otera, J. Angew. Chem., Int. Ed. 1998, 37, 91.
4. For leading examples of tandem catalysis, see: (a) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (b) Bielawski, C. W.; Louie, J. R.; Grubbs, H. J. Am. Chem. Soc. 2000, 122, 12872. (c) Drouin, S. D.; Zamanian, F.; Fogg, D. E. Organometallics 2001, 20, 5495. (d) Orita, A.; Nagano, Y.; Nakazawa, K.; Otera, J. Adv. Synth. Catal. 2002, 344, 548. (e) Chen, J.; Otera, J. Angew. Chem., Int. Ed. 1998, 37, 91.
5. For leading examples of tandem catalysis, see: (a) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (b) Bielawski, C. W.; Louie, J. R.; Grubbs, H. J. Am. Chem. Soc. 2000, 122, 12872. (c) Drouin, S. D.; Zamanian, F.; Fogg, D. E. Organometallics 2001, 20, 5495. (d) Orita, A.; Nagano, Y.; Nakazawa, K.; Otera, J. Adv. Synth. Catal. 2002, 344, 548. (e) Chen, J.; Otera, J. Angew. Chem., Int. Ed. 1998, 37, 91.
6. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994.
7. (b) Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
8. (c) Kagan, H. B. Comprehensive Organic Chemistry; Pergamon: Oxford, 1992; Vol. 8.
9. (d) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vols. I-III.
10. (e) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: New York, 2001.
11. For leading references on tandem asymmetric catalysis, see: (a) Yu, H.-B.; Hu, Q.-S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636.
12. For leading references on tandem asymmetric catalysis, see: (a) Yu, H.-B.; Hu, Q.-S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500. (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636.
13. (a) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1985, 26, 5535.
14. (b) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735.
15. Du, H.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
16. For asymmetric activation of BINOL-Zn catalysts, see: (a) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497. (b) Mikami, K.; Angelaud, R.; Ding, K.; Ishii, A.; Tanaka, A.; Sawada, N.; Kudo, K.; Senda, M. Chem. Eur. J. 2001, 7, 730. (c) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929.
17. For asymmetric activation of BINOL-Zn catalysts, see: (a) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497. (b) Mikami, K.; Angelaud, R.; Ding, K.; Ishii, A.; Tanaka, A.; Sawada, N.; Kudo, K.; Senda, M. Chem. Eur. J. 2001, 7, 730. (c) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929.
18. For asymmetric activation of BINOL-Zn catalysts, see: (a) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497. (b) Mikami, K.; Angelaud, R.; Ding, K.; Ishii, A.; Tanaka, A.; Sawada, N.; Kudo, K.; Senda, M. Chem. Eur. J. 2001, 7, 730. (c) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929.
19. For comprehensive reviews on HDA reactions, see: (a) Danishefsky, S. J.; Deninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (b) Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558. (c) Maruoka, K. In Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8A.
20. For comprehensive reviews on HDA reactions, see: (a) Danishefsky, S. J.; Deninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (b) Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558. (c) Maruoka, K. In Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8A.
21. For comprehensive reviews on HDA reactions, see: (a) Danishefsky, S. J.; Deninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (b) Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558. (c) Maruoka, K. In Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8A.
22. For reviews on combinatorial asymmetric catalysis, see: (a) Jandeleit, B.; Schaefer, D. J.; Powers, T. S., Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494. (b) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885. (c) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422. (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284. (e) Reetz, M. T.; Jaeger, K.-E. Chem. Eur. J. 2000, 6, 407. (f) Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453.
23. For reviews on combinatorial asymmetric catalysis, see: (a) Jandeleit, B.; Schaefer, D. J.; Powers, T. S., Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494. (b) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885. (c) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422. (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284. (e) Reetz, M. T.; Jaeger, K.-E. Chem. Eur. J. 2000, 6, 407. (f) Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453.
24. For reviews on combinatorial asymmetric catalysis, see: (a) Jandeleit, B.; Schaefer, D. J.; Powers, T. S., Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494. (b) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885. (c) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422. (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284. (e) Reetz, M. T.; Jaeger, K.-E. Chem. Eur. J. 2000, 6, 407. (f) Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453.
25. For reviews on combinatorial asymmetric catalysis, see: (a) Jandeleit, B.; Schaefer, D. J.; Powers, T. S., Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494. (b) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885. (c) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422. (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284. (e) Reetz, M. T.; Jaeger, K.-E. Chem. Eur. J. 2000, 6, 407. (f) Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453.
26. For reviews on combinatorial asymmetric catalysis, see: (a) Jandeleit, B.; Schaefer, D. J.; Powers, T. S., Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494. (b) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885. (c) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422. (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284. (e) Reetz, M. T.; Jaeger, K.-E. Chem. Eur. J. 2000, 6, 407. (f) Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453.
27. For reviews on combinatorial asymmetric catalysis, see: (a) Jandeleit, B.; Schaefer, D. J.; Powers, T. S., Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494. (b) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885. (c) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422. (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284. (e) Reetz, M. T.; Jaeger, K.-E. Chem. Eur. J. 2000, 6, 407. (f) Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453.