Novel Tunable CuX2-Mediated Cyclization Reaction of Cyclopropylideneacetic Acids and Esters for the Facile Synthesis of 4-Halomethyl-2(5H)-furanones and 4-Halo-5,6-dihydro-2H-pyran-2-ones

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4419-4422

  Huang, Xian ^a,b   Zhou, Hongwei ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0038614445     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026911q     Document Type: Article

References (34)

1. Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
2. (a) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3585.
3. (b) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270.
4. (c) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y J. Am. Chem. Soc. 1997, 119, 8123
5. (d) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661.
6. (e) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2002, 67, 3445.
7. (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458.
8. (g) Camacho, D. H.; Oh, B. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 2903.
9. (a) Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
10. (b) Lautens, M.; Ren, Y.; Delanghe, P. H. M. J. Am. Chem. Soc. 1994, 116, 8821.
11. (c) Oh, B. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203.
12. (d) Lautens, M.; Ren, Y. J. Am. Chem. Soc. 1996, 118, 9597.
13. (e) Lautens, M.; Ren, Y. J. Am. Chem. Soc. 1996, 118, 10668.
14. (f) Corlay, H.; Lewis, R. T.; Motherwell, W. B.; Shipman, M. Tetrahedron 1995, 51, 3303
15. (a) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015.
16. (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676.
17. (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069
18. (a) Rodebaugh, R.; Debenham, J. S.; Freiser-Reid., B.; Synder., J. P. J. Org. Chem. 1999, 64, 1758.
19. (b) Uemura, S.; Okazaki, H.; Okano, M. J. Chem. Soc., Perkin Trans. 1 1978, 1278.
20. Kortmann, I.; Werstermann, B. Synthesis 1995, 931-933.
21. Jousseaume, B.; Duboudin, J. G. Synth. Commun. 1979, 9, 53.
22. Ma, S.; Wu, S. L. J. Org. Chem. 1999, 64, 9314.
23. (a) Ma, S.; Wu, S. L. Tetrahedron Lett. 2001, 42, 4075.
24. (b) Ma, S.; Xie, H. X. J. Org. Chem. 2002, 67, 3801.
25. (a) Kawasaki, T.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2002, 67, 4911.
26. (b) Notzel, M. W.; Tamm, M.; Lahahn, T.; Notemeyer, M.; de Meijere, A. J. Org. Chem. 2000, 65, 3850.
27. (c) Zorn. C.; Goti, A.; Brandi, A.; Johnsen, K.; Notemeyer, M.; de Meijere, A. J. Org. Chem. 1999, 64, 755.
28. (d) Notzel, M. W.; Rauch, K.; Labahn, T.; de Meijere, A. Org. Lett. 2002, 4, 839.
29. (e) Notzel, M. W.; Labahn, T.; Es-sayed, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 3025.
30. (f) Zorn, C.; Anichini, B.; Goti, A.; Brandi, A.; Kozhushkov, S. I.; de Meijere, A.; Citti, L. J. Org. Chem. 1999, 64, 7846.
31. (a) Watanabe, H.; Watanabe, H.; Usui, T.; Kondoh, M.; Osada, H.; Kitahara, T. J. Antibiot. 2000, 53, 540.
32. (b) Takeda, Y.; Okeda, Y.; Masuda, T.; Hirata, E.; Shieato, T.; Takushi, A.; Yu, Q.; Otsuka, H. P. K.: Warkentin, J. Chem. Pharm. Bull. 2000, 48, 752.
33. (c) Brady, S. F.; Clardy, J. J. Nat. Prod. 2000, 63, 1447.
34. (d) Topol, I.; Burt, S. K.; Rashin, A. A.; Erickson, J. W. J. Phys. Chem. A 2000, 104, 866.