Catalytic asymmetric deprotonation using a ligand exchange approach

Journal of the American Chemical Society

Volumn 127, Issue 47, 2005, Pages 16378-16379

  McGrath, Matthew J ^a   O'Brien, Peter ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE DERIVATIVE; LIGAND; LITHIUM DERIVATIVE; PYRROLIDINE DERIVATIVE; SPARTEINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; DEPROTECTION REACTION; DISSOCIATION; ENANTIOSELECTIVITY; LIGAND EXCHAGE REACTION; LITHIATION; STOICHIOMETRY;

EID: 28444457008     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056026d     Document Type: Article

References (31)

1. Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282.
2. For a recent example, see: Zhu, J.; Grigoriadis, N. P.; Lee, J. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2005, 127, 9342.
3. (a) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
4. (b) Gittins, C. A.; North, M. Tetrahedron: Asymmetry 1997, 8, 3789.
5. (c) Alexakis, A.; Amiot, F. Tetrahedron: Asymmetry 2002, 13, 2117.
6. (a) Klein, S.; Marek, I.; Poisson, J. F.; Normam, J. F. J. Am. Chem. Soc. 1995, 117, 8853.
7. (b) Norsikian, S.; Marek, I.; Klein, S.; Poisson, J. F.; Normant, J. F. Chem.-Eur. J. 1999, 5, 2055.
8. Asano, Y.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1998, 46, 184.
9. (a) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475.
10. (b) Ferraira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
11. (c) Sigman, M. S.; Mandal, S. K. J. Org. Chem. 2003, 68, 7535.
12. (d) Bagndanoff, J. T.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 353.
13. Outside the alkyllithium/(-)-sparteine area, chiral lithium amide base-mediated catalytic asymmetric deprotonation is well studied: (a) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793.
14. (b) Yamashita, T.; Sato, D.; Kiyoto, T.: Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195.
15. (c) Södergren, M. J.; Bertilsson, S. K.; Andersson, P. G. J. Am. Chem. Soc. 2000, 112, 6610.
16. Hodgson, D. M.; Lee, G. P.; Marriott, R. E.; Thompson, A. J.; Wisedale, R.; Witherington, J. J. Chem. Soc., Perkin Trans. I 1998, 2151.
17. Beak reported this first: use of 1.3 equiv of s-BuLi and 0.25 equiv of (-)-sparteine on 1 gave (S)-2 of 64% ee and 33% yield. See: Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
18. Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870.
19. For examples of ligand exchange with (-)-sparteine, see: (a) Wilhelm, R.; Widdowson, D. A. Org. Lett. 2001, 3, 3079.
20. (b) Rutherford, J. L.; Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 2002, 124, 264.
21. Basu, A.; Thayumanavan, S. Angew. Chem., Int. Ed. 2002, 41, 716.
22. Beak had previously reported what amounts to such a ligand exchange approach: use of 1.3 equiv of s-BuLi with 0.1 equiv of (-)-sparteine and 0.9 equiv of TMEDA on 1 gave 2 of 3% ee and 64% yield (see ref 9). The lack of enantioselectivity presumably reflects the faster deprotonation of 1 by s-BuLi/TMEDA than by s-BuLi/(-)-sparteine.
23. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2005, 127, 3244.
24. O'Brien, P.; Wiberg, K. B.; Bailey, W. F.; Hermet, J.-P. R.; McGrath, M. J. J. Am. Chem. Soc. 2004, 126, 15480.
25. Asymmetric deprotonation of phosphine borane 14 has been successfully carried out using s-BuLi/diamine 12: Johansson, M. J.; Schwartz, L.; Amedjkouh, M.; Kann, N. Tetrahedron: Asymmetry 2004, 15, 3531.
26. Bispidine 13 was synthesized in two steps (see Supporting Information for full details): Garrison, G. L.; Berlin, K. D.; Scherlag, B. J.; Lazzara, R.; Patterson, E.; Fazekas, T.; Sangiah, S.; Chen, C.-L.; Schubot, F. D.; van der Helm, D. J. Med. Chem. 1996, 39, 2559.
27. Behrens, K.; Fröhlich, R.; Meyer, O.; Hoppe, D. Eur. J. Org. Chem. 1998, 2397.
28. (a) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
29. (b) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
30. (c) Wolfe, B.; Livinghouse, T. J. Org. Chem. 2001, 66, 1514.
31. Crépy, K. V. L.; Imamoto, T. Tetrahedron Lett. 2002, 43, 7735.