Highly enantioselective Pd-catalyzed allylic alkylations of acyclic ketones

Angewandte Chemie - International Edition

Volumn 44, Issue 40, 2005, Pages 6544-6546

  Yan, Xiao Xia ^a   Liang, Chun Gen ^a   Zhang, Yan ^a   Hong, Wei ^a   Cao, Bo Xun ^a   Dai, Li Xin ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkylation; Enantioselectivity; Enolates; Ketones; Palladium

Indexed keywords

ADDITION REACTIONS; ALKYLATION; CARBOXYLIC ACIDS; CATALYSIS; KETONES; MOLECULAR ORIENTATION; ORGANIC ACIDS;

ACYCLIC KETONES; ALLYLIC ALKYLATION; LEWIS ACID;

STEREOCHEMISTRY;

EID: 27144460639     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502020     Document Type: Article

References (28)

1. B. M. Trost, P. E. Strege, J. Am. Chem. Soc. 1977, 99, 1649-1651.
2. For some reviews, see: a) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422;
3. b) A. Pfaltz, M. Lautens in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Berlin, Springer, 1999, pp. 833-884;
4. c) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2944;
5. d) T. Graening, H.-G. Schmalz, Angew. Chem. 2003, 115, 2684-2688;
6. Angew. Chem. Int. Ed. 2003, 42, 2580-2584.
7. B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759-6760.
8. a) B. M. Trost, G. M. Schroeder, J. Kristensen, Angew. Chem. 2002, 114, 3642-3645;
9. Angew. Chem. Int. Ed. 2002, 41, 3492-3945;
10. b) B. M. Trost, G. M. Schroeder, Chem. Eur. J. 2005, 11, 174-184;
11. c) M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637-3640;
12. Angew. Chem. Int. Ed. 2000, 39, 3494-3497;
13. d) B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 2846-2847;
14. e) D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc 2004, 126, 15044-15045.
15. a) S.-L. You, X.-L. Hou, L.-X. Dai, X.-Z. Zhu, Org. Lett. 2001, 3, 149-151;
16. b) S.-L. You, X.-Z. Zhu, X.-L. Hou, L.-X. Dai, Acta Chim. Sin. 2001, 59, 1667-1674.
17. a) L.-X. Dai, T. Tu, S.-L. You, W.-P. Deng, X.-L. Hou, Acc. Chem. Res. 2003, 36, 659-667;
18. b) S.-L. You, X.-Z. Zhu, Y.-M. Luo, X.-L. Hou, L.-X. Dai, J. Am. Chem. Soc. 2001, 123, 7471-7472;
19. c) X.-L. Hou, N. Sun, Org. Lett. 2004, 6, 4399-4401. (Corrections: X.-L. Hou, N. Sun, Org. Lett. 2005, 7, 1435.)
20. O. Riant, O. Samuel, T. Flessner, S. Taudien, H. B. Kagan, J. Org. Chem. 1997, 62, 6733-6745.
21. J.-X. Gao, X.-D. Yi, P.-P. Xu, C.-L. Tang, H.-L. Wan, T. Ikariya, J. Organomet. Chem. 1999, 592, 290-295.
22. a) K. Muñiz, C. Bolm, Chem. Eur. J. 2000, 6, 2309-2316;
23. b) S.-L. You, X.-L. Hou, L.-X. Dai, Y. H. Yu, W. Xia, J. Org. Chem. 2002, 67, 4684-4695.
24. a) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, J. Org. Chem. 2002, 67, 7418-7423;
25. b) Y. Wang, Ph.D. Thesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 2002.
26. 6, were also tested. All of them gave the product in 68-97% yield with enantioselectivites of 76-87% ee.
27. For example: a) L. Xie, K. Vanlandeghem, K. M. Isenberger, C. Bernier, J. Org. Chem. 2003, 68, 641-643;
28. b) L. Xie, K. M. Isenberger, G. Held, L. M. Dahl, J. Org. Chem. 1997, 62, 7516-7519.