Chiral N-acylethylenediamines as new modular ligands for the catalytic asymmetric addition of alkylzinc reagents to aldehydes

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7788-7794

  Sprout, Christopher M ^a   Seto, Christopher T ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MODULAR LIGANDS;

ADDITION REACTIONS; ALCOHOLS; ALDEHYDES; BINDING ENERGY; CATALYSIS;

AROMATIC HYDROCARBONS;

2 NAPHTHALDEHYDE; 4 CHLOROBENZALDEHYDE; [2 METHYL 1 (2 MORPHOLIN 4 YLETHYLCARBAMOYL)PROPYL]CARBAMIC ACID TERT BUTYL ESTER; ALDEHYDE; BENZALDEHYDE; LIGAND; N ACYLETHYLENEDIAMINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ADDITION REACTION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; METAL BINDING; REACTION OPTIMIZATION;

EID: 0141766892     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0347516     Document Type: Article

References (47)

1. For selected reports, see: (a) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284.
2. (b) Huttenloch, O.; Laxman, E.; Waldman, H. Chem. Eur. J. 2002, 8, 4767.
3. (c) Gilbertson, S. R.; Wang, X. Tetrahedron 1999, 55, 11609.
4. (d) Burguete, M. I.; Collado, M.; García-Verdugo, E.; Vicent, M. J.; Luis, S. V.; von Keyserling, N. G.; Martens, J. Tetrahedron 2003, 59, 1797.
5. (e) Francis, M. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 937.
6. (f) Chataigner, I.; Gennari, C.; Piarulli, U.; Ceccarelli, S. Angew. Chem., Int. Ed. 2000, 39, 916.
7. (g) Cole, B. M.; Shimizu, K. D.; Kruger, C. A.; Harrity, J. P.; Snapper, M. L.; Hoveyda, A. Angew. Chem., Int. Ed. 1996, 35, 1668.
8. For reviews, see ref la and the following: Reetz, M. T. Angew. Chem., Int. Ed. 2002, 41, 1335.
9. (a) Guo, J.; Wu, J.; Siuzdak, G.; Finn, M. G. Angew. Chem., Int. Ed. 1999, 38, 1755.
10. (b) Korbel, G. A.; Lalic, G.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 361.
11. (c) Reetz, M. T.; Kuhling, K. M.; Deege, A.; Hinrichs, H.; Belder, D. Angew. Chem., Int. Ed. 2000, 39, 3891.
12. (d) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497.
13. (e) Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. 1998, 37, 2647.
14. (f) Reetz, M. T.; Zonta, A.; Schimossek, K.; Liebeton, K.; Jaeger, K.-E. Angew. Chem., Int. Ed. 1997, 36, 2830.
15. (g) Reetz, M. T.; Becker, M. H.; Klein, H.-W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758.
16. (h) Taran, F.; Gauchet, C.; Mohar, B.; Meunier, S.; Valleix, A.; Renard, P. Y.; Creminon, C.; Grassi, J.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2002, 41, 124.
17. Abato, P.; Seto, C. T. J. Am. Chem. Soc. 2001, 123, 9206.
18. This ligand architecture is related to the wide variety of ligands that have been developed by Hoveyda and Snapper. For recent examples, see: (a) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4690.
19. (b) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018.
20. (c) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 1276.
21. For reviews, see: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
22. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
23. (c) Soai, K.; Shibata, T. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 911-922.
24. (d) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
25. For selected reports, see: (a) Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
26. (b) Lutz, C.; Graf, C.-D.; Knochel, P. Tetrahedron 1998, 54, 10317.
27. (c) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 3250.
28. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. 1991, 30, 99.
29. (e) Wipf, P.; Wang, X. Org. Lett. 2002, 4, 1197.
30. (f) Ko, D.-H.; Kim, K. H.; Ha, D.-C. Org. Lett. 2002, 4, 3759.
31. (g) Nugent, W. A. Org. Lett. 2002, 4, 2133.
32. (h) Liu, D.-X.; Zhang, L.-C.; Wang, Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733.
33. (i) Dahmen, S.; Brase, S. J. Chem. Soc., Chem. Commun. 2002, 26.
34. (j) Schinneri, M.; Seitz, M.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259.
35. (k) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
36. (l) Brouwer, A. J.; Linden, H. J.; Liskamp, R. M. J. J. Org. Chem. 2000, 65, 1750.
37. When 2 equiv of diethylzinc are added to a solution of ligand 4k in toluene-ds, the IH NMR spectrum shows the disappearance of both of the NH protons and formation of ethane.
38. Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784.
39. Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003.
40. Nugent, W. A. J. Chem. Soc., Chem. Commun. 1999, 1369.
41. Cho, B. T.; Kim, N. J. Chem. Soc., Perkin Trans. 1 1996, 2901.
42. Dai, W.-M.; Zhu, H.-J.; Hao X.-J. Tetrahedron: Asymmetry 2000, 11, 2315.
43. Palmer, M. J.; Kenny, J. A.; Walsgrove, T.; Kawamoto, A. M.; Wills, M. J. Chem. Soc., Perkin Trans. 1 2002, 416.
44. Cherng, Y.-J.; Fang, J.-M.; Lu, T.-J. J. Org. Chem. 1999, 64, 3207.
45. Paquette, L. A.; Zhou, R. J. Org. Chem. 1999, 64, 7929.
46. Kwong, F. Y.; Yang, Q.; Mak, T. C. W.; Chan, A. S. C.; Chan, K. S. J. Org. Chem. 2002, 67, 2769.
47. Watanabe, M.; Araki, S.; Butsugan, Y. J. Org. Chem. 1991, 56, 2218.