Efficient coupling of allylstannane with Diels-Alder cycloadducts derived from 4-bromo-substituted masked o-benzoquinones: Synthesis of 5-allyl-oxatricyclo[m.3.1.0]decenones and undecenones

Journal of the Chinese Chemical Society

Volumn 51, Issue 5 A, 2004, Pages 1037-1042

  Lin, Ken Ching ^a   Chittimalla, Santhosh Kumar ^a   Peddinti, Rama Krishna ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

1,4 Dienes; Allylstannane; Diels Alder cycloadducts; Stille coupling

Indexed keywords

EID: 33847316638     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200400155     Document Type: Article

References (26)

1. (a) Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
2. (b) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636.
3. Reviews on Stille coupling: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
4. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998, Chapter 4.
5. (c) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87.
6. (a) Lin, S.-Y.; Chen, C.-L., Lee, Y.-J. J. Org. Chem. 2003, 68, 7551.
7. (b) Pattenden, G.; Sinclair, D. J. J. Organomet. Chem. 2002, 653, 261.
8. (c) de Meijere, A.; Zezschwitz, P. V.; Nüske, H.; Stulgies, B. J. Organomet. Chem. 2002, 653, 129.
9. (d) Paquette, L. A.; Duan, M.; Konetzki, I.; Kempmann, C. J. Am. Chem. Soc. 2002, 124, 4257.
10. (e) Marshall, J. A.; Adams, N. D. J. Org. Chem. 2002, 67, 733.
11. For recent examples, see: (a) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718.
12. (b) Huang, C.-W.; Shanmugasundaram, M.; Chang, H.-M.; Cheng, C.-H. Tetrahedron 2003, 59, 3635.
13. (c) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551.
14. (d) Gudmundsson, K. S.; Johns, B. A. Org. Lett. 2003, 5, 1369.
15. (e) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696.
16. (f) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233.
17. (g) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
18. (h) Pazos, Y.; Iglesias, B.; de Lera, A. R. J. Org. Chem. 2001, 66, 8483.
19. Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856.
20. (a) Yen, C.-F.; Liao, C.-C. Angew. Chem. Int. Ed. Engl. 2002, 41, 4090.
21. (b) Hsu, D.-S.; Liao, C.-C. Org. Lett. 2003, 5, 4741.
22. (a) Lai, C.-H.; Shen, Y.-L.; Wang, M. N.; Rao, N. S. K.; Liao, C.-C. J. Org. Chem. 2002, 67, 6493.
23. (b) Lin, K.-C.; Shen, Y.-L.; Rao, N. S. K.; Liao, C.-C. J. Org. Chem. 2002, 67, 8157.
24. Liu, W.-C.; Liao, C.-C. Synlett 1998, 912.
25. (a) Denmark, S. E.; Guagnano, V.; Dixon, J. A.; Stolle, A. J. J. Org. Chem. 1997, 62, 4610.
26. (b) Roulet, J.-M.; Deguin, B.; Vogel, P. J. Am. Chem. Soc. 1994, 116, 3639.