A simple and general chiral silicon Lewis acid for asymmetric synthesis: Highly enantioselective [3 + 2] acylhydrazone-enol ether cycloadditions

Journal of the American Chemical Society

Volumn 127, Issue 28, 2005, Pages 9974-9975

  Shirakawa, Seiji ^a   Lombardi, Pamela J ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; HYDRAZONE DERIVATIVE; LEWIS ACID; SILICON;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLOADDITION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 22244459251     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052307+     Document Type: Article

References (23)

1. For a general review of such cycloaddition reactions, see: Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford. 1991; Vol. 4, p 1111.
2. See. for example: (a) Khau, V. V.; Martinelli, M. J. Tetrahedron Lett. 1996, 37, 4323.
3. (b) Ahn, J. H.; Kim, H.-M.; Jung, S. H.; Kang, S. K.; Kim, K. R.; Rhee, S. D.; Yang, S.-D.; Cheon, H. G.; Kim S. S. Bioorg. Med. Chem. Lett. 2004, 14, 4461.
4. (a) Zlicar, M.; Stanovnik, B.; Tisler, M. Tetrahedron 1992, 48, 7965.
5. (b) Mish, M. R.; Guerra, F. M.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 8379.
6. (c) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170.
7. (d) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2661.
8. (e) Barluenga, J.; Fernández-Marí, F.; González, R.; Aguilar, E.; Revelli, G. A.; Viado, A. L.; Fañanás, F. J.; Olano, B. Eur. J. Org. Chem. 2000, 1773-1783.
9. (f) Chung, F.; Chauveau, A.; Seltki, M.; Bonin, M.; Micouin, L. Tetrahedron Lett. 2004, 45, 3127.
10. (a) Kanemasa, S.; Kanal, T. J. Am. Chem. Soc. 2000, 122, 10710.
11. (b) Shintani, R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 10778.
12. (a) Kobayashi, S.; Shimizu, H.; Yamashita, Y.; Ishitani, H.; Kobayashi, J. J. Am. Chem. Soc. 2002, 124, 13678.
13. (b) Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 11279.
14. (a) Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920.
15. (b) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946.
16. (c) Hackman, B. M.; Lombardi, P. J.; Leighton, J. L. Org. Lett. 2004, 6, 4375.
17. (d) Berger, R.; Rabbat, P. M. A.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 9596.
18. (e) Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686.
19. Shirakawa, S.; Berger. R.; Leiehton, J. L. J. Am. Chem. Soc. 2005, 127, 2858.
20. (a) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992.
21. (b) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
22. Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
23. Burk, M. J.; Martinez, J. P.; Feaster, J. E.; Cosford, N. Tetrahedron 1994, 50, 4399.