(2-methoxyphenyl)dimethylsilyl lithium and cuprate reagents offer unique advantages in multistep synthesis

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3337-3339

  Lee, Thomas W ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000533773     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0165746     Document Type: Article

References (21)

1. (a) Brook, M. A. Silicon in Organic, Organometallic and Polymer Chemistry; Wiley: New York, 2000.
2. (b) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
3. (c) Webber, W. P. Silicon Reagents in Organic Synthesis; Springer: Berlin, 1983.
4. (d) Colvin, E. W. Silicon in Organic Synthesis; Butterworths: London, 1981.
5. (e) Fleming, I.; Barbero, A.; Walker, D. Chem. Rev. 1997, 97, 2063.
6. (a) Lickiss, P. D.; Smith, C. M. Coord. Chem. Rev. 1995, 95, 75.
7. (b) Fleming, I. In Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; pp 257-292.
8. (c) George, M. V.; Peterson, D. J.; Gilman, H. J. Am. Chem. Soc. 1960, 82, 403.
9. (a) Fleming, I. Chemtracts: Org. Chem. 1996, 9, 1.
10. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
11. Rahman, N. A.; Fleming, I.; Zwicky, A. B. J. Chem. Res., Miniprint 1992, 2401.
12. (a) Müller, H.; Weinzierl, U.; Seidel, W. Z. Anorg. Allg. Chem. 1991, 603, 15.
13. (b) Weidenbruch, M.; Kramer, K. Z. Naturforsch., B: Chem. Sci. 1985, 40B, 601.
14. Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2001, 123, 1872.
15. 2SiH with n-BuLi or t-BuLi led to displacement of H by n-Bu or Me by t-Bu, respectively.
16. (a) Still, W. C. J. Org. Chem. 1976, 41, 3063.
17. (b) Hudrlik, P. F.; Waugh, M. A.; Hudrlik, A. M. J. Organomet. Chem. 1984, 271, 69.
18. (c) The HMPA/THF ratio and reactant concentration were optimized to ensure a reasonable reaction rate and a homogeneous mature at -50°C.
19. Various furylsilyl reagents have previously been applied in synthesis; see: (a) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77.
20. (b) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501.
21. (c) Stork, G. Pure Appl. Chem. 1989, 61, 439.