New carbanionic access to 3-vinylindoles and 3-vinylbenzofurans

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2791-2793

  Le Strat, Frédéric ^a   Maddaluno, Jacques ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0042190276     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026351v     Document Type: Article

References (30)

1. Inter alia: (a) Lorthiois, E.; Marek, I.; Meyer, C.; Normant, J.-F. Tetrahedron Lett. 1995, 36, 1263-1266.
2. (b) Bailey, W. F.; Punzalan, E. R. Tetrahedron Lett. 1996, 37, 5435-5436.
3. (c) Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594-2595. Enantioselective versions:
4. (d) Bailey, W. F.; Mealy, M. J. J. Am. Chem. Soc. 2000, 122, 6787-6788.
5. (e) Sanz Gil, G.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790.
6. (f) Ashweek, N. J.; Coldham, I.; Snowden, D. J.; Vennall, G. P. Chem. Eur. J. 2002, 8, 195-207.
7. Johnson, F.; Subramanian, R. J. Org. Chem. 1986, 51, 5041-5043.
8. Normant, J.-F.; Alexakis, A. Synthesis 1981, 841-870.
9. (a) Kandil, S. A.; Dessy, R. E. J. Am. Chem. Soc. 1966, 88, 3027-3034.
10. (b) Ward, H. R. J. Am. Chem. Soc. 1967, 89, 5517-5518.
11. Wu, G.; Cederbaum, F. E.; Negishi, E. Tetrahedron Lett. 1990, 31, 493-496.
12. Inter alia: (a) Bailey, W. F.; Ovaska, T. V.; Leipert, T. K. Tetrahedron Lett. 1989, 30, 3901-3904.
13. (b) Bailey, W. F.; Ovaska, T. V. Tetrahedron Lett. 1990, 31, 627-630.
14. (c) Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080-3090.
15. (d) Bailey, W. F.; Aspris, P. H. J. Org. Chem. 1995, 60, 754-757.
16. (e) Bailey, W. F.; Wachter-Jurcsak, N. M.; Pineau, M. R.; Ovaska, T. V.; Warren, R. R.; Lewis, C. E. J. Org. Chem. 1996, 61, 8216-8228.
17. Bailey, W. F.; Ovaska, T. V. Chem. Lett. 1993, 819-820.
18. Krief, A.; Remacle, B.; Mercier, J. Synlett 2000, 1443-1446.
19. (a) Guillam, A.; Toupet, L.; Maddaluno, J. J. Org. Chem. 1998, 63, 5110-5122.
20. (b) Guillam, A.; Toupet, L.; Maddaluno, J. J. Org. Chem. 1999, 64, 9348-9357.
21. (c) Le Strat, F.; Maddaluno, J. Tetrahedron Lett. 2000, 41, 5367-5371.
22. A related intermediate lithiated benzofurane has been recently proposed: Barluenga, J.; Fañnás, F. J.; Sanz, R.; Marcos, C. Org. Lett. 2002, 4, 2225-2228.
23. See for instance: (a) Saroja, B.; Srinivasan, P. C. Synthesis 1986, 748-749.
24. (b) Eberle, M. K.; Shapiro, M. J.; Stucki, R. J. Org. Chem. 1987, 52, 4661-4665.
25. (c) Pindur, U. Heterocycles 1988, 27, 1253-1268.
26. (d) Kraus, G. A.; Thomas, P. J.; Bougie, D.; Chen, L. J. Org. Chem. 1990, 55, 1624-1627.
27. (e) Pearson, J. R.; Porter, Q. N. Aust. J. Chem. 1991, 44, 1085-1095.
28. (f) Sundberg, R. J. Indoles; Academic Press: London, UK, 1996.
29. (g) Kinsman, A. C.; Kerr, M. A. Org. Lett. 2001, 3, 3189-3191.
30. Jenner, G. Tetrahedron 1997, 53, 2669-2695.