Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl) cyclobutanols with aryl iodides. Stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones

Organic Letters

Volumn 6, Issue 12, 2004, Pages 1979-1982

  Yoshida, Masahiro ^a   Sugimoto, Kenji ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1,3 BUTADIENYL)CYCLOBUTANOL; 2 [3 (1 PROPENYL)CYCLOPENTANONE]; ALCOHOL DERIVATIVE; CYCLOPENTANONE DERIVATIVE; IODIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 3042710770     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049438k     Document Type: Article

References (47)

1. (a) Tsuji, J. Palladium Reagents and Catalysts; John Wiley and Sons: New York, 1995.
2. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
3. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
4. (a) Patel, B. A.; Dickerson, J. E.; Heck, R. F. J. Org. Chem. 1978, 43, 5018.
5. (b) Patel, B. A.; Kao, L. C.; Cortese, N. A.; Minkiewicz, J. V.; Heck, R. F. J. Org. Chem. 1979, 44, 918.
6. (c) Stakem, F. G.; Heck, R. F. J. Org. Chem. 1980, 45, 3584.
7. (d) Fischetti, W.; Mak, K. T.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1983, 48, 948.
8. (e) O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
9. (f) Uno, M.; Takahashi, T.; Takahashi, S. Chem. Commun. 1987, 785.
10. (g) Grigg, R.; Sridharan, V. Tetrahedron Lett. 1989, 30, 1139.
11. (h) Larock, R. C.; Fried, C. A. J. Am. Chem. Soc. 1990, 112, 5882.
12. (i) Larock, R. C.; Berrios-Pena, N. G.; Narayanan, K. J. Org. Chem. 1990, 55, 3447.
13. (j) Larock, R. C.; Berrios-Pena, N. G.; Fried, C. A.; Yum, E. K.; Tu, C.; Leong, W. J. Org. Chem. 1993, 58, 4509.
14. (k) Kagechika, K.; Ohshima T.; Shibasaki. M. Tetrahedron 1993, 49, 1773.
15. (l) Ohshima, T.; Kagechika, K.; Adachi, A.; Sodeoka, M.; Shibasaki. M. J. Am. Chem. Soc. 1996, 118, 7108.
16. (m) Flubacher, D.; Helmchen, G. Tetrahedron Lett. 1999, 40, 3867.
17. (n) Deagostino, A.; Prandi, C.; Venturello, P. Org. Lett. 2003, 5, 3815.
18. (a) Boontanonda, P.; Grigg, R. J. Chem. Soc., Chem. Commun. 1977, 583.
19. (b) Clark, G. R.; Thiensathit, S. Tetrahedron Lett. 1985, 26, 2503.
20. (c) Demuth, M.; Pandey, B.; Wietfeld, B.; Said, H.; Viader, J. Helv. Chim. Acta 1988, 71, 1392.
21. (d) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177.
22. (e) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1991, 32, 3395.
23. (f) Nemoto, H.; Miyata, J.; Fukumoto, K. Tetrahedron 1996, 52, 10363.
24. (g) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Chem. Soc. Perkin Trans. 1 1993, 2329.
25. (h) Nemoto, H.; Nagamochi, M.; Ishibashi, H.; Fukumoto, K. J. Org. Chem. 1994, 59, 74.
26. (i) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933.
27. (j) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517.
28. (k) Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645.
29. (a) Nemoto, H.; Shiraki, M.; Fukumoto, K. Synlett 1994, 599.
30. (b) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850.
31. (c) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907.
32. (d) Yoshida, M.; Ismail, M. A.-H.; Nemoto, H.; Ihara, M. J. Chem. Soc., Perkin Trans, 1 2000, 2629.
33. (a) Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 6450.
34. (b) Yoshida, M.; Sugimoto, K.; Ihara, M. Tetrahedron Lett. 2000, 41, 5089.
35. (c) Yoshida, M.; Sugimoto, K.; Ihara, M. Tetrahedron 2002, 58, 7839.
36. (d) Yoshida, M.; Sugimoto, K.; Ihara, M. Tetrahedron Lett. 2001, 42, 3877.
37. (a) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908.
38. (b) Mitchell, D.; Liebeskind L. S. J. Am. Chem. Soc. 1990, 112, 291.
39. (c) Larock, R. C.; Reddy, Ch. K. Org. Lett. 2000, 2, 3325.
40. (d) Larock, R. C.; Reddy, Ch. K. J. Org. Chem. 2002, 67, 2027.
41. (e) Yoshida, M.; Sugimoto, K.; Ihara, M. ARKIVOC 2003, xiii, 35.
42. Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583.
43. For studies about the diastereoselectivity in the ring expansion reaction of cyclobutanols, see refs 4b-d, 5b,c, and 7.
44. As another possibility, the intermediate that palladium cation forms a bond to the alkoxide anion is also expected.
45. The conformation of (Z)-1·5 was predicted from the result of MOPAC 97/PM3 calculation of (Z)-1a.
46. (a) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
47. (b) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.