Zinc-mediated chain extension reaction of 1,3-diketones to 1,4-diketones and diastereoselective synthesis of trans-1,2-disubstituted cyclopropanols

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 215-218

  Xue, Song ^a   Li, Le Zhen ^a   Liu, Yong Kang ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; KETONES; SYNTHESIS (CHEMICAL);

CYCLOPROPANOLS; DIASTEREOSELECTIVITY; ORGANOZINC SPECIES;

AROMATIC HYDROCARBONS;

1,3 DIKETONE; 1,4 DIKETONE; PROPANOL; ZINC;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 31144433644     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051950b     Document Type: Article

References (53)

1. (a) Mussatto, M. C.; Savoia, D.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1980, 45, 4002.
2. (b) Rao, A. V. R.; Deshpande, V. H.; Reddy, S. P. Synth. Commun. 1984, 14, 469.
3. (c) Takahashi, K.; Aihara, T.; Ogura, K. Chem. Lett. 1987, 2359.
4. (d) Pecuniso, A.; Menicagli, R. J. Org. Chem. 1988, 53, 2614.
5. (e) Fiandanese, V.; Marchese, G.; Naso, F. Tetrahedron Lett. 1988, 29, 3587.
6. (f) Bergman, R.; Nilsson, B.; Wickberg, B. Tetrahedron 1990, 31, 2783.
7. (a) Wenkert, E.; Buckwalter, B. L.; Craveiro, A. A.; Sanchez, E. L.; Sathe, S. S. J. Am. Chem. Soc. 1978, 100, 1267.
8. (b) Wenkert, E.; Greenberg, R. S.; Ragu, M. S. J. Org. Chem. 1985, 50, 4681.
9. (c) Curran, D. P. Tetrahedron 1994, 58, 1181.
10. (d) Roberts, S. M.; Santoro, M. G.; Sickle J. J. Chem. Soc., Perkin Trans. 1 2002, 1735.
11. (e) Banik, B. K.; Banik, I.; Renteria, M.; Dasgupta, S. K. Tetrahedron Lett. 2005, 46, 2643.
12. (a) Liu, Y. G.; Zhang, Y. M. Tetrahedron. 2003, 59, 8429.
13. (b) Ho, T. L. Polarity Control for Synthesis; Wiley: New York, 1991; Chapter 7.
14. (c) Amarnath, V.; Douglas, C. A.; Amarnath, K.; Valentine, W. M.; Wetteran, L. A.; Graham, D. G. J. Org. Chem. 1991, 56, 6924.
15. (a) Finch, N.; Fitt, J. J.; Hsu, I. H. C. J. Org. Chem. 1971, 36, 3191.
16. (b) Negishi, E.-I.; Luo, F.-T.; Pecora, A. J.; Silveira, A., Jr. J. Org. Chem. 1983, 48, 2427.
17. (c) Rosini, G.; Ballini, R.; Sorrenti, P. Tetrahedron 1983, 39, 4127.
18. (d) Pecunioso, A.; Menicagli, R. J. Org. Chem. 1988, 53, 2614.
19. (e) Arcadi, A.; Cacchi, S.; Marinelli, F.; Misiti, D. Tetrahedron Lett. 1988, 29, 1457.
20. (f) Miyashita, M.; Yanami, T.; Kumazawa, T.; Yoshikoshi, A. J. Am. Chem. Soc. 1984, 106, 2149.
21. (a) Bergman, R.; Nilsson, R.; Wickberg, B. Tetrahedron Lett. 1990, 31, 2783.
22. (b) Freeman, F.; Kim, D. S. H. J.; Rodriguez, E. J. Org. Chem. 1992, 57, 1722.
23. (c) Wedler, C.; Schick, H. Synthesis 1992, 543.
24. (c) Yuguchi, M.; Tokuda, M.; Orito, K. J. Org. Chem. 2004, 69, 908.
25. (a) Lu, X. Y.; Ji, J. G.; Ma, D. W.; Shen, W. J. Org. Chem. 1991, 56, 5774.
26. (b) Huang, J.-T.; Su, T.-L.; Watanabe, K. A. J. Org. Chem. 1991, 56, 4811.
27. (c) Katritzky, A. R.; Zhang, G. F.; Jiang, J. L. J. Org. Chem. 1995, 60, 7605.
28. (d) Matsumoto, S.; Okubo, Y.; Mikami, K. J. Am. Chem. Soc. 1998, 120, 4015.
29. (e) Yasuda, M.; Tsuji, S.; Shigeyoshi, Y.; Baba, A. J. Am. Chem. Soc. 2002, 124, 7440.
30. (f) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
31. (a) Brogan, J, B.; Zercher, C. K. J. Org. Chem. 1997, 62, 6444.
32. (b) Ronsheim, M. D.; Hilgenkamp, R.; Zercher, C. K. Org. Synth. 2002, 79, 146.
33. (c) Lai, S.; Zercher, C. K.; Jasinski, J. P.; Reid, S. N.; Staples, R. J. Org. Lett. 2001, 3, 4169.
34. (d) Hilgenkamp, R.; Zercher, C. K. Org. Lett. 2001, 3, 3037.
35. (e) Ronsheim, M. D.; Zercher, C. K. J. Org. Chem. 2003, 68, 4535.
36. Hilgenkamp, R.; Zercher, C. K. Tetrahedron 2001, 57, 8793.
37. Verbicky, C. A.; Zercher, C. K. J. Org. Chem. 2000, 65, 5615.
38. Mu, X. J.; Zou, J. P.; Wang, Z. T.; Zhang, W. Tetrahedron Lett. 2005, 46, 4727.
39. (a) Xue, S.; Li, Y. L.; Han, K. Z.; Yin, W.; Wang, M.; Guo, Q. X. Org. Lett. 2002, 4, 905.
40. (b) Xue, S.; He, L.; Han, K. Z.; Liu, Y. K.; Guo, Q. X. Synlett 2005, 8, 1247.
41. (c) Xue, S.; Liu, Y. K.; Li, L. Z.; Guo, Q. X. J. Org. Chem. 2005, 70, 8245.
42. (a) Yang, Z.; Lorenz, J. C.; Shi, Y. Tetrahedron Lett. 1998, 39, 8621.
43. (b) Lorenz, J. C.; Long, J.; Yang, Z. Q.; Xue, S.; Xie, Y. N.; Shi, Y. J. Org. Chem. 2004, 69, 327.
44. See the Supporting Information for details.
45. (a) De Puy, C. H. Acc. Chem. Res. 1968, 1, 33.
46. (b) Salaun, J. Top. Curr. Chem. 1988, 144, 1.
47. (c) Salaun, J. Chem. Rev. 1989, 89, 1247.
48. (d) Kulinkovich, O. G. Chem. Res. 2003, 103, 2597.
49. (a) Liu, H. U.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: London, 1987; p 959.
50. (b) Suckling, C. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 537.
51. (c) Salaun, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
52. (d) Salaun, J. Top. Curr. Chem. 2000, 207, 1.
53. 2I with 1-phenylbutane-1,3-dione gave 7a in 63% yield along with a 31% yield of the chain-extended product 2c.