Mild α-fluorination of enantiomerically pure β-ketosulfoxides by F-TEDA-BF4

Journal of Fluorine Chemistry

Volumn 84, Issue 1, 1997, Pages 79-82

  Arnone, Alberto ^a   Bravo, Pierfrancesco ^b   Frigerio, Massimo ^b   Salani, Giuliana ^b   Viani, Fiorenza ^a   Zanda, Matteo ^b   Zappalà, Carmela ^b  

^a CNR   (Italy)

^b Riconoscimento Molecolare   (Italy)

Author keywords

Chiral sulfoxides; F TEDA BF4; Fluorination

Indexed keywords

EID: 0031592775     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(97)00035-3     Document Type: Article

References (30)

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9. For recent reviews see R.E. Banks, J.C. Tatlow, B.E. Smart, Organofluorine Chemistry: Principles and Commercial Applications, Plenum, New York, 1994; G. Resnati, V.A. Soloshonok (Eds.), Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Tetrahedron Symposium-in-Print N. 58, Tetrahedron 52 (1996) 1-330.
10. J.R. McCarthy, N.P. Peet, M.E. Le Tourneau, M. Inbasekaran, J. Am. Chem. Soc. 107 (1985) 735. M. Robins, S.F. Wnuk, J. Org. Chem. 55 (1990) 4757; P. Herdewijn, A. De Bruyn, P. Wigerinck, C. Hendrix, L. Kerremans, J. Rozenski, R. Busson, J. Chem. Soc. Perkin Trans. I (1994) 249; L.S. Jeong, V.E. Marquez, Chem. Lett. (1995) 301. For other fluorinations of sulfoxides see M.J. Robins, S.F. Wnuk, K.B. Mullah, N.K. Dalley, C.-S. Yuan, Y. Lee, R.T. Borchardt, J. Org. Chem. 59 (1994) 544; J. Chiba, T. Sugihara, C. Kaneko, Chem. Lett. (1995) 581.
11. J.R. McCarthy, N.P. Peet, M.E. Le Tourneau, M. Inbasekaran, J. Am. Chem. Soc. 107 (1985) 735. M. Robins, S.F. Wnuk, J. Org. Chem. 55 (1990) 4757; P. Herdewijn, A. De Bruyn, P. Wigerinck, C. Hendrix, L. Kerremans, J. Rozenski, R. Busson, J. Chem. Soc. Perkin Trans. I (1994) 249; L.S. Jeong, V.E. Marquez, Chem. Lett. (1995) 301. For other fluorinations of sulfoxides see M.J. Robins, S.F. Wnuk, K.B. Mullah, N.K. Dalley, C.-S. Yuan, Y. Lee, R.T. Borchardt, J. Org. Chem. 59 (1994) 544; J. Chiba, T. Sugihara, C. Kaneko, Chem. Lett. (1995) 581.
12. J.R. McCarthy, N.P. Peet, M.E. Le Tourneau, M. Inbasekaran, J. Am. Chem. Soc. 107 (1985) 735. M. Robins, S.F. Wnuk, J. Org. Chem. 55 (1990) 4757; P. Herdewijn, A. De Bruyn, P. Wigerinck, C. Hendrix, L. Kerremans, J. Rozenski, R. Busson, J. Chem. Soc. Perkin Trans. I (1994) 249; L.S. Jeong, V.E. Marquez, Chem. Lett. (1995) 301. For other fluorinations of sulfoxides see M.J. Robins, S.F. Wnuk, K.B. Mullah, N.K. Dalley, C.-S. Yuan, Y. Lee, R.T. Borchardt, J. Org. Chem. 59 (1994) 544; J. Chiba, T. Sugihara, C. Kaneko, Chem. Lett. (1995) 581.
13. J.R. McCarthy, N.P. Peet, M.E. Le Tourneau, M. Inbasekaran, J. Am. Chem. Soc. 107 (1985) 735. M. Robins, S.F. Wnuk, J. Org. Chem. 55 (1990) 4757; P. Herdewijn, A. De Bruyn, P. Wigerinck, C. Hendrix, L. Kerremans, J. Rozenski, R. Busson, J. Chem. Soc. Perkin Trans. I (1994) 249; L.S. Jeong, V.E. Marquez, Chem. Lett. (1995) 301. For other fluorinations of sulfoxides see M.J. Robins, S.F. Wnuk, K.B. Mullah, N.K. Dalley, C.-S. Yuan, Y. Lee, R.T. Borchardt, J. Org. Chem. 59 (1994) 544; J. Chiba, T. Sugihara, C. Kaneko, Chem. Lett. (1995) 581.
14. J.R. McCarthy, N.P. Peet, M.E. Le Tourneau, M. Inbasekaran, J. Am. Chem. Soc. 107 (1985) 735. M. Robins, S.F. Wnuk, J. Org. Chem. 55 (1990) 4757; P. Herdewijn, A. De Bruyn, P. Wigerinck, C. Hendrix, L. Kerremans, J. Rozenski, R. Busson, J. Chem. Soc. Perkin Trans. I (1994) 249; L.S. Jeong, V.E. Marquez, Chem. Lett. (1995) 301. For other fluorinations of sulfoxides see M.J. Robins, S.F. Wnuk, K.B. Mullah, N.K. Dalley, C.-S. Yuan, Y. Lee, R.T. Borchardt, J. Org. Chem. 59 (1994) 544; J. Chiba, T. Sugihara, C. Kaneko, Chem. Lett. (1995) 581.
15. J.R. McCarthy, N.P. Peet, M.E. Le Tourneau, M. Inbasekaran, J. Am. Chem. Soc. 107 (1985) 735. M. Robins, S.F. Wnuk, J. Org. Chem. 55 (1990) 4757; P. Herdewijn, A. De Bruyn, P. Wigerinck, C. Hendrix, L. Kerremans, J. Rozenski, R. Busson, J. Chem. Soc. Perkin Trans. I (1994) 249; L.S. Jeong, V.E. Marquez, Chem. Lett. (1995) 301. For other fluorinations of sulfoxides see M.J. Robins, S.F. Wnuk, K.B. Mullah, N.K. Dalley, C.-S. Yuan, Y. Lee, R.T. Borchardt, J. Org. Chem. 59 (1994) 544; J. Chiba, T. Sugihara, C. Kaneko, Chem. Lett. (1995) 581.
16. P. Bey, J.R. McCarthy, I.A. McDonald, Terminal fluoroolefins, in: J.T. Welch (Ed.), Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symp. Ser., Washington, DC, 1991, pp. 105-133; J.R. McCarthy, E.T. Jarvi, D.P. Matthews, M.L. Edwards, N.J. Prakash, T.L. Bowlin, S. Mehdi, P.S. Sunkara, P. Bey, J. Am. Chem. Soc. 111 (1989) 1127.
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18. 4 see G.S. Lal, J. Org. Chem. 58 (1993) 2791; M. Zupan, J. Iskra, S. Stavber, J. Org. Chem. 60 (1995) 259; J. Wang, I. Scott, J. Chem. Soc. Chem. Commun. (1995) 2399.
19. 4 see G.S. Lal, J. Org. Chem. 58 (1993) 2791; M. Zupan, J. Iskra, S. Stavber, J. Org. Chem. 60 (1995) 259; J. Wang, I. Scott, J. Chem. Soc. Chem. Commun. (1995) 2399.
20. 4 see G.S. Lal, J. Org. Chem. 58 (1993) 2791; M. Zupan, J. Iskra, S. Stavber, J. Org. Chem. 60 (1995) 259; J. Wang, I. Scott, J. Chem. Soc. Chem. Commun. (1995) 2399.
21. 4 see G.S. Lal, J. Org. Chem. 58 (1993) 2791; M. Zupan, J. Iskra, S. Stavber, J. Org. Chem. 60 (1995) 259; J. Wang, I. Scott, J. Chem. Soc. Chem. Commun. (1995) 2399.
22. 4 see G.S. Lal, J. Org. Chem. 58 (1993) 2791; M. Zupan, J. Iskra, S. Stavber, J. Org. Chem. 60 (1995) 259; J. Wang, I. Scott, J. Chem. Soc. Chem. Commun. (1995) 2399.
23. 4 see G.S. Lal, J. Org. Chem. 58 (1993) 2791; M. Zupan, J. Iskra, S. Stavber, J. Org. Chem. 60 (1995) 259; J. Wang, I. Scott, J. Chem. Soc. Chem. Commun. (1995) 2399.
24. For leading references on the synthesis and the chemistry of chiral fluorinated sulfoxides see A. Arnone, P. Bravo, A. Donadelli, G. Resnati, Tetrahedron 52 (1996) 131; T. Satoh, K. Takano, Tetrahedron 52 (1996) 2349; V. Reutrakul, T. Kruahong, M. Pohmakotr, Tetrahedron Lett. 35 (1994) 4853. For a review on 1-haloalkyl aryl sulfoxides see T. Satoh, K. Yamakawa, Synlett (1992) 455.
25. For leading references on the synthesis and the chemistry of chiral fluorinated sulfoxides see A. Arnone, P. Bravo, A. Donadelli, G. Resnati, Tetrahedron 52 (1996) 131; T. Satoh, K. Takano, Tetrahedron 52 (1996) 2349; V. Reutrakul, T. Kruahong, M. Pohmakotr, Tetrahedron Lett. 35 (1994) 4853. For a review on 1-haloalkyl aryl sulfoxides see T. Satoh, K. Yamakawa, Synlett (1992) 455.
26. For leading references on the synthesis and the chemistry of chiral fluorinated sulfoxides see A. Arnone, P. Bravo, A. Donadelli, G. Resnati, Tetrahedron 52 (1996) 131; T. Satoh, K. Takano, Tetrahedron 52 (1996) 2349; V. Reutrakul, T. Kruahong, M. Pohmakotr, Tetrahedron Lett. 35 (1994) 4853. For a review on 1-haloalkyl aryl sulfoxides see T. Satoh, K. Yamakawa, Synlett (1992) 455.
27. For leading references on the synthesis and the chemistry of chiral fluorinated sulfoxides see A. Arnone, P. Bravo, A. Donadelli, G. Resnati, Tetrahedron 52 (1996) 131; T. Satoh, K. Takano, Tetrahedron 52 (1996) 2349; V. Reutrakul, T. Kruahong, M. Pohmakotr, Tetrahedron Lett. 35 (1994) 4853. For a review on 1-haloalkyl aryl sulfoxides see T. Satoh, K. Yamakawa, Synlett (1992) 455.
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30. A. Arnone, P. Bravo, S. Capelli, G. Fronza, S.V. Meille, M. Zanda, G. Cavicchio, M. Crucianelli, J. Org. Chem. 61 (1996) 3375.