Polystyrene-bound cinchona alkaloids: Application to enantioselective electrophilic fluorination of silyl enol ethers

Synlett

Volumn , Issue 5, 2004, Pages 856-860

  Thierry, Baptiste ^a   Audouard, Christophe ^a   Plaquevent, Jean Christophe ^a   Cahard, Dominique ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

Cinchona alkaloids; Electrophilic fluorination; Enantioselective synthesis; Polymer

Indexed keywords

AMMONIA; CINCHONA ALKALOID; POLYSTYRENE; SILANE DERIVATIVE;

ARTICLE; ENANTIOSELECTIVITY; FLUORINATION; STEREOCHEMISTRY;

EID: 1942489329     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817781     Document Type: Article

References (30)

1. (a) Muñiz, K. Angew. Chem. Int. Ed. 2001, 40, 1653.
2. (b) Muñiz, K. Organic Synthesis Highlights, Vol. 5; Schmalz, H.-G.; Wirth, T., Eds.; Wiley-VCH: Weinheim, 2003, 201-209.
3. (a) Cahard, D.; Audouard, C.; Plaquevent, J. C.; Roques, N. Org. Lett. 2000, 2, 3699.
4. (b) Cahard, D.; Audouard, C.; Plaquevent, J. C.; Toupet, L.; Roques, N. Tetrahedron Lett. 2001, 42, 1867.
5. (c) Mohar, B.; Baudoux, J.; Plaquevent, J. C.; Cahard, D. Angew. Chem. Int. Ed. 2001, 40, 4214.
6. (d) Baudequin, C.; Plaquevent, J. C.; Audouard, C.; Cahard, D. Green Chem. 2002, 4, 584.
7. (e) Zoute, L.; Audouard, C.; Plaquevent, J. C.; Cahard, D. Org. Biomol. Chem. 2003, 1, 1833.
8. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
9. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
10. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
11. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
12. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
13. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
14. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
15. + reagents, see: (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494. (d) By means of transition metal catalysts: Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (e) See also: Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. (f) See further: Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225. (g) By phase-transfer catalysis: Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (h) By fluorodesilylation: Greedy, B.; Paris, J. M.; Vidai, T.; Gouverneur, V. Angew. Chem. Int. Ed. 2003, 42, 3291.
16. (a) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
17. (b) Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J. C.; Cahard, D. Synthesis 2001, 11, 1742.
18. (c) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2003, 14, 1671.
19. (a) Banks, R. E.; Tsiliopoulos, E. J. Fluorine Chem. 1986, 34, 281.
20. (b) Umemoto, T.; Nagayoshi, M.; Adachi, K.; Tomizawa, G. J. Org. Chem. 1998, 63, 3379.
21. Song, C. E.; Roh, E. J.; Lee, S.-g.; Kim, I. O. Tetrahedron: Asymmetry 1995, 6, 2687.
22. 3: C, 76.03; H, 7.06; N, 6.14; O, 10.51. Found: C, 76.33; H, 7.33; N, 5.87; O, 10.47.
23. (a) Hermann, K.; Wynberg, H. Helv. Chim. Acta 1977, 60, 2208.
24. (b) Aglietto, M.; Chiellini, E.; D'Antone, S.; Ruggeri, G.; Solaro, R. Pure Appl. Chem. 1988, 60, 415.
25. (c) Dannelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, P.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461.
26. Heidelberger, M.; Jacobs, W. A. J. Am. Chem. Soc. 1919, 41, 817.
27. Braje, W.; Frackenpohl, J.; Langer, P.; Hoffmann, H. M. R. Tetrahedron 1998, 54, 3495.
28. Braje, W. M.; Frackenpohl, J.; Schrake, O.; Wartchow, R.; Beil, W.; Hoffmann, H. M. R. Helv. Chim. Acta 2000, 83, 777.
29. Baudequin, C.; Loubassou, J. F.; Plaquevent, J. C.; Cahard, D. J. Fluorine Chem. 2003, 122, 189.
30. 2O, 9:1), leading to the fluorinated ketone 2b (see ref. 2d for spectroscopic data). The enantiomeric excess was then determined by HPLC using Chiracel OB column.