Highly regio-, diastereo-, and enantioselective Pd-catalyzed allylic alkylation of acyclic ketone enolates with monosubstituted allyl substrates

Journal of the American Chemical Society

Volumn 129, Issue 25, 2007, Pages 7718-7719

  Zheng, Wen Hua ^a   Zheng, Bao Hui ^a   Zhang, Yan ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; KETONE; PALLADIUM;

ALKYLATION; ARTICLE; ASYMMETRIC ALLYLIC ALKYLATION; CATALYSIS; ENANTIOSELECTIVITY; LIGAND BINDING; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 34347252945     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071098l     Document Type: Article

References (34)

1. For reviews: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
2. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 2, p 833.
3. (c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
4. For examples: (a) Hayashi, T.; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561.
5. (b) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.
6. (c) Prétôt, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323.
7. (d) Hilgraf, R.; Pfaltz, A. Synlett 1999, 1814.
8. (a) Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659.
9. (b) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471.
10. (c) Hou, X.-L.; Sun, N. Org. Lett. 2004, 6, 4399; corrections: Org. Lett. 2005, 7, 1435.
11. (d) Zheng, W. H.; Sun, N.; Hou, X. L. Org. Lett. 2005, 7, 5151.
12. For examples using other metal catalysts in regio- and enantioselective allylic alkylation: (a) Evans, P. A.; Leahy, D. K. J. Am. Chem. Soc. 2000, 122, 5012.
13. (b) Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
14. (c) Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 116.
15. (d) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164.
16. (e) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104.
17. Some examples using simple ketone enolates as nucleophile in Pd-catalyzed AAA: (a) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759.
18. (b) Braun, M.; Laicher, F.; Meier, T. Angew. Chem., Int. Ed. 2000, 39, 3494.
19. (c) Kazmaier, U. Curr. Org. Chem. 2003, 7, 317.
20. (d) Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc 2004, 126, 15044.
21. (e) Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113.
22. (f) Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 2846.
23. (g) Trost, B. M.; Schroeder, G. M. Chem. - Eur. J. 2005, 11, 174.
24. (h) Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 17180.
25. (i) Trost, B. M.; Xu, J.; Reichle, M. J. Am. Chem. Soc. 2007, 129, 282.
26. (j) Bélanger, E.; Cantin, K.; Messe, O.; Tremblay, M.; Paquin, J-F. J. Am. Chem. Soc. 2007, 129, 1034.
27. (a) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Zhu, X.-Z. Org. Lett. 2001, 3, 149.
28. (b) Yan, X. X.; Liang, C. G.; Zhang, Y.; Hong, W.; Cao, B. X.; Dai, L. X.; Hou, X. L. Angew. Chem., Int. Ed. 2005, 44, 6544.
29. Excellent example of other metal-catalyzed AAA using ketone enolates: Graening, T.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 17192.
30. (a) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635.
31. (b) Trost, B. M.; Dogra, K. J. Am. Chem. Soc. 2002, 124, 7256.
32. Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054.
33. Evans, P. A.; Lawler, M. J. J. Am. Chem. Soc. 2004, 126, 8642.
34. Wang, D. Z.; Kim, Y.-J.; Streitwieser, A. J. Am. Chem. Soc. 2000, 122, 10754.