Regio- and stereoselective heck arylations of N-carbomethoxy-L-3- dehydroproline methyl ester with arenediazonium salts. Total synthesis of neuroexcitatory aryl kainoids

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2815-2818

  Da Silva, Kezia Peixoto ^a   Godoi, Marla Narciso ^a   Correia, Carlos Roque Duarte ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547196841     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070980t     Document Type: Article

References (32)

1. (a) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.: Wiley: Hoboken, NJ, 2002.
2. (b) Palladium Reagents and Catalysis; Tsuji, J., Ed.; Wiley: Chichester, UK, 1995.
3. (a) Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.
4. (b) Tietze, L.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453.
5. For a review of Pd-catalyzed cross-coupling reactions using diazonium salts, see: Roglans, A.; Pla-Quintana, A.; Moreno-Mañas, M. Chem. Rev. 2006, 106, 4622.
6. Garcia, A. L. L.; Carpes, M. J. S.; Montes de Oca, A. C. B.; Santos, M. A. G.; Santana, C. C.; Correia, C. R. D. J. Org. Chem. 2005, 70, 1050.
7. (a) Crisp, G. T.; Gebauer, M. G. Tetrahedron 1996, 52, 12465.
8. (b) Evans, P. J. Org. Chem. 2007, 72, 1830. Evans attempts to carry out Heck arylation of a L-3-dehydroproline derivative yielded mainly 2-carboethoxy pyrrole.
9. (a) Maeda, K.; Kadama, T.; Tanaka, T.; Yoshiziemi, H.; Takemoto, T.; Nomoto. K.; Fujita, T. Chem. Pharm. Bull. 1986, 34, 4892.
10. (b) Shinozaki, H.; Ishida, M.; Okamoto, T. Brain Res. 1986, 399, 395.
11. (c) Ishida, M.; Shinozaki, H. Brain Res. 1988, 474, 386.
12. (d) For a review, consult: Parsons, A. F. Tetrahedron 1996, 52, 4149.
13. (a) Itadami, S.; Takai, S.; Tanigawa, C.; Hashimoto, K.; Shirahama, H. Tetrahedron Lett. 2002, 43, 7777.
14. (b) Ahmed, A.; Bragg, R. A.; Clayden, J.; Tchabanenko, K. Tetrahedron Lett. 2001, 42, 3407.
15. (c) Bragg, R. A.; Clayden, J.; Bladon, M.; Ichihara, O. Tetrahedron Lett. 2001, 42, 3411.
16. (d) Maeda, H.; Selvakumar, N.; Kraus, G. A. Tetrahedron 1999, 55, 943.
17. (e) Maeda. H.; Kraus, G. A. J. Org. Chem. 1997, 62, 2314.
18. (f) Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Whitehead, R. C.; Wood, M. E. Tetrahedron Lett. 1996, 37, 6923.
19. (g) Hashimoto, K.; Shirahama, H. Tetrahedron Lett. 1991, 32, 2625.
20. (h) Hashimoto, K.; Horikawa, M.; Shirahama, H. Tetrahedron Lett. 1990, 31, 7047.
21. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzen, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996. 118, 6826.
22. Shono, T.; Matsumura, Y.; Inoue, K. J. Chem. Soc., Chem. Commun. 1983, 1169.
23. Oliveira, D. F.; Miranda, P. C. L.; Correia, C. R. D. J. Org. Chem. 1999, 64, 6446.
24. At present, reaction conditions were optimized only for arenediazonium containing the p-OMe, o-OMe, and p-Cl.
25. Deeth, R. J.; Smith, A.; Brown, J. M. J. Am. Chem. Soc. 2004, 126, 7144.
26. This assumption is precedented in the work of Deeth and co-workers (ref 12). It is also conceivable that such a model would explain the results obtained by Crisp and Evans (ref 5).
27. (a) Ezquerra, J.; Escribano, A.; Rubio, A.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron: Asymmetry 1996, 7, 2613.
28. (b) Ezquerra, J.; Escribano, A.; Rubio, A.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1995, 36, 6149.
29. 3J = 7.8 Hz), suggesting a C-2, C-3 trans relationship, as described by Shirahama (ref 6b). The stereochemistry of the substituents at C-3 and C-4 can be established by the empirical rules proposed by Baldwin and Shirahama: (a) Baldwin, J. E.; Fryer, A. M.; Pritchard, G. J. J. Org. Chem. 2001, 66, 2597.
30. (b) Hashimoto, K.; Konno, K.; Shirahama, H. J. Org. Chem. 1996, 61, 4685.
31. Attempts to perform hydrolysis under basic conditions led to a mixture of the all cis diester with its C-2 epimer in a 1:1 ratio.
32. Klotz, P.: Mann, A. Tetrahedron Lett. 2003, 44, 1927.