Highly enantioselective propargylic monofluorination established by carbon-13 and fluorine-19 NMR in chiral liquid crystals

Chemical Communications

Volumn , Issue 2, 2000, Pages 169-170

  Madiot, Valérie ^a   Lesot, Philippe ^b   Grée, Danielle ^a   Courtieu, Jacques ^b   Gree, René ^a  

^a UNIV RENNES   (France)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 13; FLUORINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; FLUORINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0034695504     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909012f     Document Type: Article

References (21)

1. See for instance: J. T. Welch, Tetrahedron, 1987, 43, 3123; Selective Fluorination in Organic and Bioorganic Chemistry, ed. J. T. Welch, ACS symposium series 456, Washington DC, 1991; Biomedical Frontiers of Fluorine Chemistry, ed. I. Ojima, J. R. McCarthy and J. T. Welch, ACS symposium series 639, Washington DC, 1996.
2. See for instance: J. T. Welch, Tetrahedron, 1987, 43, 3123; Selective Fluorination in Organic and Bioorganic Chemistry, ed. J. T. Welch, ACS symposium series 456, Washington DC, 1991; Biomedical Frontiers of Fluorine Chemistry, ed. I. Ojima, J. R. McCarthy and J. T. Welch, ACS symposium series 639, Washington DC, 1996.
3. See for instance: J. T. Welch, Tetrahedron, 1987, 43, 3123; Selective Fluorination in Organic and Bioorganic Chemistry, ed. J. T. Welch, ACS symposium series 456, Washington DC, 1991; Biomedical Frontiers of Fluorine Chemistry, ed. I. Ojima, J. R. McCarthy and J. T. Welch, ACS symposium series 639, Washington DC, 1996.
4. R. L. Gree and J. P. Lellouche, Enantiocontrolled Synthesis of Fluoro-Organic Compounds, ed. V. A. Soloshonok, Wiley, Chichester, 1999.
5. D. M. Gree, C. J. M. Kermarrec, J. T. Martelli, R. L. Gree, J. P. Lellouche and L. J. Toupet, J. Org. Chem., 1996, 61, 1918; C. Kermarrec, V. Madiot, D. Gree, A. Meyer and R. Gree, Tetrahedron Lett., 1996, 37, 5691; S. Legoupy, C. Crevisy, J. C. Guillemin and R. Gree, J. Fluorine Chem., 1999, 93, 171.
6. D. M. Gree, C. J. M. Kermarrec, J. T. Martelli, R. L. Gree, J. P. Lellouche and L. J. Toupet, J. Org. Chem., 1996, 61, 1918; C. Kermarrec, V. Madiot, D. Gree, A. Meyer and R. Gree, Tetrahedron Lett., 1996, 37, 5691; S. Legoupy, C. Crevisy, J. C. Guillemin and R. Gree, J. Fluorine Chem., 1999, 93, 171.
7. D. M. Gree, C. J. M. Kermarrec, J. T. Martelli, R. L. Gree, J. P. Lellouche and L. J. Toupet, J. Org. Chem., 1996, 61, 1918; C. Kermarrec, V. Madiot, D. Gree, A. Meyer and R. Gree, Tetrahedron Lett., 1996, 37, 5691; S. Legoupy, C. Crevisy, J. C. Guillemin and R. Gree, J. Fluorine Chem., 1999, 93, 171.
8. F. A. Davis and P. V. N. Kasu, Tetrahedron Lett., 1998, 39, 6135.
9. F. Diederich and P. J. Stang, Metal-catalysed Cross-coupling Reactions, Wiley, Weinheim, 1998
10. For a synthesis of stereodefined systems with allylic fluorides (V. Madiot, D. Gree and R. Gree, Tetrahedron Lett., 1999, 40, 6403).
11. Few propargylic monofluorides have been described, see: (a) C. D. Poulter, P. L. Wiggins and T. L. Plummer, J. Org. Chem., 1981, 46, 1532;
12. (b) F. Benayoud, D. J. de Mendonca, C. A. Digits, G. A. Moniz, T. C. Sanders and G. B. Hammond, J. Org. Chem., 1996, 61, 5159;
13. (c) T. Munyemana, PhD Thesis, Louvain la Neuve, Belgium, 1991.
14. Only two optically active compounds have been previously reported, see: Y. Matsumura, T. Shimada, T. Nakayama, M. Urushirara, T. Asai, Y. Morizawa and A. Yasuda, Tetrahedron, 1995, 51, 8771.
15. For exceptions, see: R. E. A. Dear and E. E. Gilbert, J. Org. Chem., 1968, 33, 819. See also ref. 7(b).
16. The isolated yields are rather low due to the volatility of this type of derivative.
17. I. Canet, J. Courtieu, A. Loewenstein, A. Meddour and J. M. Péchiné, J. Am. Chem. Soc., 1995, 117, 6520.
18. A. Meddour, P. Berdagué, A. Hedli, J. Courtieu and P. Lesot, J. Am. Chem. Soc., 1997, 119, 4502.
19. M. Jakubcova, A. Meddour, J. M. Péchiné, A. Baklouti and J. Courtieu, J. Fluorine Chem., 1997, 86, 149.
20. M. Hudlicky, Org. React., 1988, 35, 516.
21. For the n-octyl derivative, see: F. Baludri, V. Fiandanese, O. Hassan, A. Punzi and F. Naso, Tetrahedron, 1998, 54, 4327.