Regioselective lithiation of silyl phosphine sulfides: asymmetric synthesis of p-stereogenic compounds

Organic Letters

Volumn 11, Issue 21, 2009, Pages 5022-5025

  Gammon, Jonathan J ^a   O'Brien, Peter ^a   Kelly, Brian ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b Celtic Catalysts Ltd   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70350678976     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901977p     Document Type: Article

References (23)

1. (a) Crépy, K. V. L.; Imamoto, T. Adv. Synth. Catal. 2003, 345, 79.
2. (b) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1.
3. (c) Tang, W.; Zhang, X. Chem. Rev. 2003,103, 3029.
4. (d) Zhang, W.; Chi, Y.; Zhang, X. Acc. Chem. Res. 2007, 40, 1278.
5. (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375.
6. (b) Grabulosa, A.; Granell, J.; Muller, G. Coord. Chem. Rev. 2007, 251, 25.
7. (c) Glueck, D. S. Chem.-Eur. J. 2008, 14, 7108.
8. Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
9. (a) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
10. (b) Gridnev, I. D.; Yamanoi, Y.; Higashi, N.; Tsuruta, H.; Yasutake, M.; Imamoto, T. Adv. Synth. Catal. 2001, 343, 118.
11. Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988.
12. Johansson, M. J.; Andersson, K. H. O.; Kann, N. J. Org. Chem. 2008, 73, 4458.
13. (a) Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002,124, 11870.
14. (b) O'Brien, P. Chem. Commun. 2008, 655.
15. (a) Johansson, M. J.; Schwartz, L. O.; Amedjkouh, M.; Kann, N. C. Eur. J. Org. Chem. 2004, 1894.
16. (b) Johansson, M. J.; Schwartz, L. O.; Amedjkouh, M.; Kann, N. Tetrahedron: Asymmetry 2004, 15, 3531.
17. Genet, G; Canipa, S. J.; O'Brien, P.; Taylor, S. J. Am. Chem. Soc. 2006, 128, 9336.
18. We have assigned phosphine sulfide 4 in Scheme 1 with (R)configuration. This assumes that the CH2E substituent is of higher priority in the Cahn-Ingold-Prelog rules than the R and CH3 groups.
19. Crépy, K. V. L.; Imamoto, T. Tetrahedron Lett. 2002, 43, 7735.
20. Gammon, J. J.; Canipa, S. J.; O'Brien, P.; Kelly, B.; Taylor, S. Chem. Commun. 2008, 3750.
21. The sense of induction obtained by direct lithiation of phosphine sulfide 5 using ra-BuLi/(-)-sparteine is known (see ref 11).
22. Imamoto, T.; Sugita, K.; Yoshida, K. J. Am. Chem. Soc. 2005,127, 11934.
23. Hoge, G.; Wu, H.-P.; Kissel, W. S.; Pflum, D. A.; Greene, D. J.; Bao, J. J. Am. Chem. Soc. 2004, 126, 5966.