Realization of high regioselectivity in the coupling reaction of a cyclopentadiene monoepoxide equivalent and aryl nucleophiles

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 597-600

  Kobayashi, Yuichi ^a   Takahisa, Eisuke ^a   Usmani, Shahid B ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; HYDROXYL GROUP; LITHIUM DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; ISOMERISM; STEREOSPECIFICITY;

EID: 0032510007     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10654-2     Document Type: Article

References (33)

1. 1b (cf ref 1c). To the best of our knowledge, the reaction of the better (see Text) substrate 2 with organocoppers is not reported. (a) Marino, J. P.; Farina, J. S. J. Org. Chem. 1976, 41, 3213-3215.
2. (b) Marino, J. P.; Kelly, M. G. J. Org. Chem. 1981, 46, 4389-4393.
3. (c) Marino, J. P.; Fernández de la Pradilla, R.; Laborde, E. J. Org. Chem. 1987, 52, 4898-4913.
4. (d) Tucci, F. C; Chieffi, A.; Comasseto, J. V.; Marino, J. P. J. Org. Chem. 1996, 61, 4975-4989.
5. 2. (a) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969-5972.
6. (b) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343.
7. (c) Oppolzer, W.; Gaudin, J.-M.; Birkinshaw, T. N. Tetrahedron Lett. 1988, 29, 4705-4708.
8. (d) Mori, M.; Nukui, S.; Shibasaki, M. Chem. Lett. 1991, 1797-1800.
9. (e) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016-2021.
10. (f) Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776-5788.
11. (g) Mazón, A.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron Lett. 1997, 38, 2167-2170.
12. 3. Tueting, D. R.; Echavarren, A. M.; Stille, J. K. Tetrahedron 1989, 45, 979-992.
13. 4. (a) Miyaura, N.; Tanabe, Y.; Suginome, H.; Suzuki, A. J. Organometal. Chem. 1982, 233, C13-C16,
14. (b) Larock, R. C.; Ding, S. J. Org. Chem. 1993, 58, 804-806.
15. (c) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825-826.
16. (d) White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1995, 117, 6224-6233.
17. (e) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C. Synth. Commun. 1997, 27, 1267-1271.
18. (f) Marshall, J. A. Chem. Rev. 1989, 89, 1503-1511 and references cited therein.
19. 5. Kobayashi, Y.; Watatani, K.; Kikori, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 6125-6128.
20. 6. See the references cited in the following letter.
21. 3Ph], under a variety of conditions using the nickel and palladium catalysts mentioned in the text. However, no coupling product(s) was obtained.
22. 8. Kobayashi, Y.; Mizojiri, R.; Ikeda, E. J. Org. Chem. 1996, 61, 5391-5399.
23. 9. Similar tendency for phenylstannane is reported in the Stille coupling with alkenyl inflates: Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033-3040.
24. 10. Deardorff, D. R.; Myles, D. C. In Organic Syntheses; Freeman, J. P., Ed.; Wiley: New York, 1993; Collect. Vol. 8, pp 13-16.
25. 10. Deardorff, D. R.; Myles, D. C. In Organic Syntheses; Freeman, J. P., Ed.; Wiley: New York, 1993; Collect. Vol. 8, pp 13-16.
26. 11b of 3a or 4a to 8.
27. (b) Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160-5165.
28. 12. Suzuki, M.; Oda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623-1625.
29. 3;(2) LiOH], respectively.
30. 14. Ratios of 6a/7a obtained with the nitriles were 5.2 (MeCN), 3.9 (EtCN), 4.0 (PhCN), and 6.0 (AIBN), respectively.
31. 9,15a-cHowever, these salts did not improve the regioselectivity in question. (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486.
32. (b) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
33. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444.