Stereoselective synthesis of internal allylic fluorides

Organic and Biomolecular Chemistry

Volumn 2, Issue 8, 2004, Pages 1110-1112

  Thibaudeau, Sébastien ^a   Fuller, Robert ^a   Gouverneur, Véronique ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; ISOMERS; NUCLEAR MAGNETIC RESONANCE; RUTHENIUM; STEREOCHEMISTRY; STYRENE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CROSS METATHESIS (CM) REACTIONS; FLUORINATED PRODUCTS; NUCLEOPHILIC DISPLACEMENT; STEREOSELECTIVITY;

FLUORINE COMPOUNDS;

EID: 2342532375     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b402097a     Document Type: Article

References (27)

1. For general reviews on the physical properties of fluorinated compounds: B. E. Smart, in Chemistry of Organic Fluorine Compounds II: A Critical Review, M. Hudlicky and A. E. Pavlath, Eds., ACS Monograph 187, American Chemical Society, Washington, DC, 1995; pp 979-1010; B. E. Smart, in Organofluorine Chemistry: Principles and Commercial Applications, R. E. Banks, B. E. Smart and J. C. Tatlow, Eds., Plenum Publishing Corporation: New York, 1994; pp 57-88;. For applications of organofluorine compounds in pharmaceutical development, see for example: P. N. Edwards, in Organofluorine Chemistry: Principles and Commercial Applications; R. E. Banks, B. E. Smart and J. C.Tatlow, Eds., Plenum Publishing Corporation, New York, 1994, pp 501-541; I. Ojima, J. R. Mc Carthy and J. T. Welch, Eds., Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639, American Chemical Society, Washington, 1996; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry; John Wiley and Sons, New York, 1991.
2. For general reviews on the physical properties of fluorinated compounds: B. E. Smart, in Chemistry of Organic Fluorine Compounds II: A Critical Review, M. Hudlicky and A. E. Pavlath, Eds., ACS Monograph 187, American Chemical Society, Washington, DC, 1995; pp 979-1010; B. E. Smart, in Organofluorine Chemistry: Principles and Commercial Applications, R. E. Banks, B. E. Smart and J. C. Tatlow, Eds., Plenum Publishing Corporation: New York, 1994; pp 57-88;. For applications of organofluorine compounds in pharmaceutical development, see for example: P. N. Edwards, in Organofluorine Chemistry: Principles and Commercial Applications; R. E. Banks, B. E. Smart and J. C.Tatlow, Eds., Plenum Publishing Corporation, New York, 1994, pp 501-541; I. Ojima, J. R. Mc Carthy and J. T. Welch, Eds., Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639, American Chemical Society, Washington, 1996; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry; John Wiley and Sons, New York, 1991.
3. For general reviews on the physical properties of fluorinated compounds: B. E. Smart, in Chemistry of Organic Fluorine Compounds II: A Critical Review, M. Hudlicky and A. E. Pavlath, Eds., ACS Monograph 187, American Chemical Society, Washington, DC, 1995; pp 979-1010; B. E. Smart, in Organofluorine Chemistry: Principles and Commercial Applications, R. E. Banks, B. E. Smart and J. C. Tatlow, Eds., Plenum Publishing Corporation: New York, 1994; pp 57-88;. For applications of organofluorine compounds in pharmaceutical development, see for example: P. N. Edwards, in Organofluorine Chemistry: Principles and Commercial Applications; R. E. Banks, B. E. Smart and J. C.Tatlow, Eds., Plenum Publishing Corporation, New York, 1994, pp 501-541; I. Ojima, J. R. Mc Carthy and J. T. Welch, Eds., Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639, American Chemical Society, Washington, 1996; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry; John Wiley and Sons, New York, 1991.
4. For general reviews on the physical properties of fluorinated compounds: B. E. Smart, in Chemistry of Organic Fluorine Compounds II: A Critical Review, M. Hudlicky and A. E. Pavlath, Eds., ACS Monograph 187, American Chemical Society, Washington, DC, 1995; pp 979-1010; B. E. Smart, in Organofluorine Chemistry: Principles and Commercial Applications, R. E. Banks, B. E. Smart and J. C. Tatlow, Eds., Plenum Publishing Corporation: New York, 1994; pp 57-88;. For applications of organofluorine compounds in pharmaceutical development, see for example: P. N. Edwards, in Organofluorine Chemistry: Principles and Commercial Applications; R. E. Banks, B. E. Smart and J. C.Tatlow, Eds., Plenum Publishing Corporation, New York, 1994, pp 501-541; I. Ojima, J. R. Mc Carthy and J. T. Welch, Eds., Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639, American Chemical Society, Washington, 1996; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry; John Wiley and Sons, New York, 1991.
5. For general reviews on the physical properties of fluorinated compounds: B. E. Smart, in Chemistry of Organic Fluorine Compounds II: A Critical Review, M. Hudlicky and A. E. Pavlath, Eds., ACS Monograph 187, American Chemical Society, Washington, DC, 1995; pp 979-1010; B. E. Smart, in Organofluorine Chemistry: Principles and Commercial Applications, R. E. Banks, B. E. Smart and J. C. Tatlow, Eds., Plenum Publishing Corporation: New York, 1994; pp 57-88;. For applications of organofluorine compounds in pharmaceutical development, see for example: P. N. Edwards, in Organofluorine Chemistry: Principles and Commercial Applications; R. E. Banks, B. E. Smart and J. C.Tatlow, Eds., Plenum Publishing Corporation, New York, 1994, pp 501-541; I. Ojima, J. R. Mc Carthy and J. T. Welch, Eds., Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639, American Chemical Society, Washington, 1996; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry; John Wiley and Sons, New York, 1991.
6. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
7. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
8. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
9. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
10. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
11. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
12. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
13. W. J. Middelton, J. Org. Chem., 1975, 40, 574-578; S. De Jonghe, I. Van Overmeire, S. Poulton, C. Hendrix, R. Busson, S. Van Calenbergh, D. De Keukeleire, S. Spiegel and P. Herdewijn, Bioorg. Med. Chem. Lett., 1999, 9, 3175-3180; F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345; M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 1991, 32, 6355; R. L. Grée J. P. Lellouche, in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets, V. A. Soloshonok, ed., Wiley, New York, 1999; pp. 535-556; M. Prakesh, D. Grée and R. Grée, J. Org. Chem., 2001, 66, 3146; D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Perez and K. N. Houk, J. Org. Chem., 2001, 66, 2374; V. Madiot, D. Grée and R. Grée, Tetrahedron Lett., 1999, 40, 6403; M. Prakesh, D. Grée and R. Grée, Acc. Chem. Res., 2002, 35, 175; M. Prakesh, D. Grée and R. Grée, Tetrahedron, 2003, 59, 8833; D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J. P. Llelouche and L. Toupet, J. Org. Chem., 1996, 61, 1918.
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27. 2: 268.1338, found 268.1326.