Efficient stereochemical controllers in biaryl Suzuki coupling reactions: Benzylic carbinols bearing in β-position thioether, dimethylamino, or sulfoxide groups

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3737-3740

  Broutin, Pierre Emmanuel ^a   Colobert, Françoise ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24044438182     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051382m     Document Type: Article

References (44)

1. Bringmann, G.; Gunther, C.; Ochse, M.; Schupp, O.; Tasler, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Tamm, C., Eds; Springer: New York, 2001; Vol. 82.
2. (a) Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon Press: New York, 1991; Vol. 3, p 481.
3. (b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
4. (c) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879-881.
5. (d) Meyers, A. I.; Himmelsbach, R. J. J. Am. Chem. Soc. 1985, 107, 682-685.
6. (e) Wilson, J. M.; Cram, D. J. J. Org. Chem. 1984, 49, 4930-4943.
7. (f) Wilson, J. M.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 881-884.
8. (g) Feldmann, K. S.; Smith, R. S. J. Org. Chem. 1996, 61, 2606-2612.
9. (h) Saito, S.; Kano, T.; Muto, H.; Nakadai, M.; Yamamoto, H. J. Am. Chem. Soc. 1999, 121, 8943-8944.
10. ( i) Lin, G.-G.; Zhong, M. Tetrahedron: Asymmetry 1997, 8, 1369-1372.
11. (j) Brusse, J.; Groenendijk, J. L. G.; te Copele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313-3319.
12. (k) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 10, 8153-8156.
13. (l) Hayashi, T.; Hayashizaki, K.; Ito, Y. Tetrahedron Lett. 1989, 30, 215-218.
14. (m) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101-9102.
15. (n) Kamikawa, T.; Hayashi, T. Tetrahedron 1999, 55, 3455-3466.
16. Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T.-Y.; Natarajan, S.; Chu, X.-J.; Bräse, S.; Rübsam, F. Chem. Eur. J. 1999, 5, 2584-2601.
17. (a) Cammidge, A. N.; Crepy, K. V. L.Chem. Commun. 2000, 1723-1724.
18. (b) Cammidge, A. N.; Crepy, K. V. L. Tetrahedron 2004, 60, 4377-4386.
19. Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052.
20. Herrbach, A.; Marinetti, A.; Baudoin, O.; Guenard, D.; Gueritte, F. J. Org. Chem. 2003, 12, 4897-4905.
21. Jensen, J. F.; Johannsen, M. Org. Lett. 2003, 5, 3025-3028.
22. Mikami, K.; Miyamoto, T.; Hatano, M. Chem. Commun. 2004, 2082-2083.
23. Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659-665.
24. Kamikawa, K.; Uemura, M. Synlett 2000, 938-949.
25. Lipshutz, B. H.; Keith, J. M. Angew. Chem., Int. Ed. 1999, 38, 3530-3533.
26. (a) Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281-3284.
27. (b) Broutin, P.-E.; Colobert, F. Eur. J. Org. Chem. 2005, 1113-1128.
28. Solladié, G.; Carreño, M. C. In Organosulfur Chemistry: Synthetic Aspects; Page, P. C. B., Ed.; Academic Press: New York, 1995; pp 1-47.
29. Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 13, 2009-2012.
30. Kupchan, S. M.; Britton, R. W.; Ziegler, M. F.; Gilmore, C. J.; Restivo, R. J.; Brian, R. F. J. Am. Chem. Soc. 1973, 95, 1335-1336.
31. Hallock, Y. F.; Manfredi, K. P.; Blunt, J. W.; Cardellina, J. H. II; Schâffer, M.; Gulden, K. P.; Bringmann, G.; Lee, A. Y.; Clardy, J.; François, G.; Boyd, M. R. J. Org. Chem. 1994, 59, 6349-6355.
32. Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172-1193.
33. Arnone, A.; Bravo, P.; Farina, A.; Frigerio, M.; Valdo Meille, S.; Viani, F. Tetrahedron: Asymmetry 1995, 6, 2695-2707.
34. Hirth, U. H.; Springler, B.; Wirth, T. J. Org. Chem. 1998, 63, 7674-7679.
35. Sugihara, H.; Tanikaga, R.; Kaji, A. Synthesis 1978, 881.
36. Bravo, P.; Frigerio, M.; Resnati, G. J. Org. Chem. 1990, 55, 4216-4218.
37. Petitou, M.; Duchaussoy, P.; Choay, J. Tetrahedron Lett. 1988, 29, 1389-1390.
38. Hugues, D. L.; Org. React. 1992, 42, 335-656.
39. Bayley, H.; Standring, D. N.; Knowles, J. R. Tetrahedron Lett. 1978, 19, 3633-3634.
40. (a) Pine, S. H.; Sanchez, B. L. J. Org. Chem. 1971, 36, 829-832.
41. (b) Brunet, E.; Gallego, M. T.; Garcia Ruano, J. L.; Alcudia, F. Tetrahedron 1986, 42, 1423-1438.
42. (a)Grennberg, H.; Gogoll, A.; Bäckvall, J.-E. J. Org. Chem. 1991, 56, 5808-5811.
43. (b) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502.
44. (c) Garcia-Ruano, J. L.; Gonzalez, A. M.; Lopez-Solera, I.; Masaguer, J. R.; Navarro-Ranninger, C.; Raithby, P. R.; Rodriguez, J. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1351.