First enantio-flexible fluorination reaction using metal-bis(oxazoline) complexes

Synlett

Volumn , Issue 10, 2004, Pages 1703-1706

  Shibata, Norio ^a   Ishimaru, Takehisa ^a   Nagai, Tatsuya ^a   Kohno, Junji ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric catalysis; Copper; Fluorine; Halogenation; Nickel

Indexed keywords

COPPER; METAL; NICKEL; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; FLUORINATION;

EID: 4143150689     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829571     Document Type: Article

References (41)

1. Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions; Ramachandran, P. V., Ed.; ACS Symposium Series 746, American Chemical Society: Washington DC, 2000.
2. (a) Differding, E.; Lang, R. W. Tetrahedron Lett. 1988, 29, 6087.
3. (b) Davis, F. A.; Han, W. Tetrahedron Lett. 1991, 32, 1631.
4. (c) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przeslawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273.
5. (d) Takeuchi, Y.; Suzuki, T.; Satoh, A.; Shiragami, T.; Shibata, N. J. Org. Chem. 1999, 64, 5708.
6. (e) Shibata, N.; Liu, Z.; Takeuchi, Y. Chem. Pharm. Bull. 2000, 48, 1954.
7. (f)Liu, Z.; Shibata, N.; Takeuchi, Y. J. Org. Chem. 2000, 65, 7583.
8. (a) Muniz, K. Angew. Chem. Int. Ed. 2001,40, 1653.
9. (b) Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359.
10. (c) Piana, S.; Devillers, I.; Togni, A.; Rothlisberger, U. Angew. Chem. Int. Ed. 2002, 41, 979.
11. (d) Togni, A.; Mezzetti, A.; Barthazy, P.; Becker, C.; Devillers, I.; Frantz, R.; Hintermann, L.; Perseghini, M.; Sanna, M. Chimia 2000, 55, 801.
12. (e) Cahard, D.; Audouard, C.; Plaquevent, J.-C.; Roques, N. Org. Lett. 2000, 2, 3699.
13. (f) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem. Int. Ed. 2001, 40, 4214.
14. (g) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545.
15. (h) Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530.
16. (a) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728.
17. (b) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001.
18. (c) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494.
19. (d) Shibata, N. Pharmacia 2003, 39, 666.
20. Bruns, S.; Haufe, G. J. Fluorine Chem. 2000, 104, 247.
21. (a) Kim, Y. H. Acc. Chem. Res. 2001, 34, 955.
22. (b) Sibi, M. P.; Liu, M. Curr. Org. Chem. 2001, 5, 719.
23. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999.
24. 2-bis(oxazoline) metal complexes as catalysts, see for example: (a) Ghosh, A. K.; Mathivanen, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605. Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407. Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558. (e) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
25. 2-bis(oxazoline) metal complexes as catalysts, see for example: (a) Ghosh, A. K.; Mathivanen, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605. Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407. Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558. (e) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
26. 2-bis(oxazoline) metal complexes as catalysts, see for example: (a) Ghosh, A. K.; Mathivanen, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605. (c) Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407. Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558. (e) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
27. 2-bis(oxazoline) metal complexes as catalysts, see for example: (a) Ghosh, A. K.; Mathivanen, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605. (c) Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407. (d) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558. (e) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
28. 2-bis(oxazoline) metal complexes as catalysts, see for example: (a) Ghosh, A. K.; Mathivanen, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605. (c) Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407. (d) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558. (e) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
29. (a) Nakamura, S.; Nakagawa, R.; Watanabe, Y.; Toru, T. Angew. Chem. Int. Ed. 2000, 39, 353.
30. (b) Nakamura, S.; Nakagawa, R.; Watanabe, Y.; Toru, T. J. Am. Chem. Soc. 2000, 122, 11340.
31. Just before the submission of this manuscript, Cu(II)-bis(oxazoline)- catalyzed halogenations have been reported: (a) Enantioselective fluorination reaction using Cu(II)-bis(oxazoline): Ma, J.-A.; Canard, D. Tetrahedron: Asymmetry 2004, 15, 1007. (b) Enantioselective bromination and chlorination reactions using Cu(II)-bis(oxazoline): Marigo, M.; Kumaragurubaran, N.; Jørgensen, K. A. Chem.-Eur. J. 2004, 10, 2133.
32. Just before the submission of this manuscript, Cu(II)-bis(oxazoline)- catalyzed halogenations have been reported: (a) Enantioselective fluorination reaction using Cu(II)-bis(oxazoline): Ma, J.-A.; Canard, D. Tetrahedron: Asymmetry 2004, 15, 1007. (b) Enantioselective bromination and chlorination reactions using Cu(II)-bis(oxazoline): Marigo, M.; Kumaragurubaran, N.; Jørgensen, K. A. Chem.-Eur. J. 2004, 10, 2133.
33. (a) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706.
34. (b) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394.
35. (c) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355.
36. (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, C. R. Tetrahedron Lett. 1999, 40, 2879.
37. (b) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635.
38. (c) Thorhauge, J.; Roberson, M.; Hazell, R. G.; Jørgensen, K. A. Chem.-Eur. J. 2002, 8, 1888.
39. Although we tentatively speculate the geometry of the metal centers as shown in Figure 2, they can be changed depending on the conditions, counter anions and substrates. Geometry optimizations are under being performed by MO calculations and X-ray crystallographic studies of the intermediates.
40. 4 and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with hexane-EtOAc to give the fluorinated product. The ee of the product was determined by chiral HPLC on CHIRALPAK AD-H column.
41. After this work was submitted the Ru(II)-catalyzed asymmetric fluorination of β-ketoesters with NFSI using N,N′-bis{o-[bis(phenyl) phosphino]benzylidene}-(1S,2S)-diaminocyclohexane was briefly reported in the review. See: Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147.