The first enantiocontrolled synthesis of E,E conjugated dienes with a fluorine atom in the allylic position

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1918-1919

  Gree, Danielle M ^a   Kermarrec, Christophe J M ^a   Martelli, Jacques T ^a   Gree, René L ^a   Lellouche, Jean Paul ^b   Toupet, Loïc J ^c  

^a CNRS   (France)

^b CEA SACLAY   (France)

^c UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ORGANOFLUORINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029870633     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9601270     Document Type: Article

References (49)

1. German, L.; Zemskov, S. New Fluorinating Agents in Organic Synthesis: Springer Verlag: Berlin, 1989. Knunyants, I. L.; Yakobson, G. G. Syntheses of Fluoroorganic Compounds; Springer Verlag: Berlin, 1987.
2. German, L.; Zemskov, S. New Fluorinating Agents in Organic Synthesis: Springer Verlag: Berlin, 1989. Knunyants, I. L.; Yakobson, G. G. Syntheses of Fluoroorganic Compounds; Springer Verlag: Berlin, 1987.
3. Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982. Mann, J. Chem. Soc. Rev. 1987, 16, 381 Welch, J. T. Tetrahedron 1987, 43, 3123. Welch, J. T.; Eswarakrishnan, S. Fluorine in Biorganic Chemistry; Wiley Interscience: New York, 1991. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991. Abeles, R. H.; Alston, T. A. J. Biol. Chem 1990, 265, 16705.
4. Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982. Mann, J. Chem. Soc. Rev. 1987, 16, 381 Welch, J. T. Tetrahedron 1987, 43, 3123. Welch, J. T.; Eswarakrishnan, S. Fluorine in Biorganic Chemistry; Wiley Interscience: New York, 1991. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991. Abeles, R. H.; Alston, T. A. J. Biol. Chem 1990, 265, 16705.
5. Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982. Mann, J. Chem. Soc. Rev. 1987, 16, 381 Welch, J. T. Tetrahedron 1987, 43, 3123. Welch, J. T.; Eswarakrishnan, S. Fluorine in Biorganic Chemistry; Wiley Interscience: New York, 1991. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991. Abeles, R. H.; Alston, T. A. J. Biol. Chem 1990, 265, 16705.
6. Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982. Mann, J. Chem. Soc. Rev. 1987, 16, 381 Welch, J. T. Tetrahedron 1987, 43, 3123. Welch, J. T.; Eswarakrishnan, S. Fluorine in Biorganic Chemistry; Wiley Interscience: New York, 1991. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991. Abeles, R. H.; Alston, T. A. J. Biol. Chem 1990, 265, 16705.
7. Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982. Mann, J. Chem. Soc. Rev. 1987, 16, 381 Welch, J. T. Tetrahedron 1987, 43, 3123. Welch, J. T.; Eswarakrishnan, S. Fluorine in Biorganic Chemistry; Wiley Interscience: New York, 1991. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991. Abeles, R. H.; Alston, T. A. J. Biol. Chem 1990, 265, 16705.
8. Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982. Mann, J. Chem. Soc. Rev. 1987, 16, 381 Welch, J. T. Tetrahedron 1987, 43, 3123. Welch, J. T.; Eswarakrishnan, S. Fluorine in Biorganic Chemistry; Wiley Interscience: New York, 1991. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991. Abeles, R. H.; Alston, T. A. J. Biol. Chem 1990, 265, 16705.
9. See, for instance: Rozen, S.; Filler, R. Tetrahedron 1985, 41, 1111. Bravo, P.; Resnati, G. Tetrahedron Asymmetry 1990, 1, 661. Hewitt, C. D., Silvester, M. J. Aldrichim Acta 1988, 21, 3.
10. See, for instance: Rozen, S.; Filler, R. Tetrahedron 1985, 41, 1111. Bravo, P.; Resnati, G. Tetrahedron Asymmetry 1990, 1, 661. Hewitt, C. D., Silvester, M. J. Aldrichim Acta 1988, 21, 3.
11. See, for instance: Rozen, S.; Filler, R. Tetrahedron 1985, 41, 1111. Bravo, P.; Resnati, G. Tetrahedron Asymmetry 1990, 1, 661. Hewitt, C. D., Silvester, M. J. Aldrichim Acta 1988, 21, 3.
12. For a recent example, see Piva, O. Synlett 1994, 729.
13. Middleton, W. J. J. Org. Chem. 1975, 40, 574. Hudlicky, M. Org. React. New York 1988, 36, 513.
14. Middleton, W. J. J. Org. Chem. 1975, 40, 574. Hudlicky, M. Org. React. New York 1988, 36, 513.
15. Middleton, W. J. US Patent 3914265, 1975. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Chem. Commun. 1981, 511.
16. Bezuglov, V. V.; Bergelson, L. D. Bioorg. Khim. 1979, 5, 1531 (Engl. transl. 1137).
17. Paaren, H. E.; Fivizzani, M. A.; Schnoes, H. K.; Deluca, H. F. Arch. Biochem. Biophys. 1981, 209, 579.
18. Canfarini, F.; Giolitti, A.; Guidi, A.; Pasqui, F.; Pestellini, V.; Arcamone, F. Tetrahedron Lett. 1993, 34, 4697. Jeong, L. S.; Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett, 1994, 35, 7569.
19. Canfarini, F.; Giolitti, A.; Guidi, A.; Pasqui, F.; Pestellini, V.; Arcamone, F. Tetrahedron Lett. 1993, 34, 4697. Jeong, L. S.; Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett, 1994, 35, 7569.
20. Franck-Neumann, M. Organametallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 247. Pearson, A. J. Acc. Chem. Res. 1980, 13, 463. Pearson, A. J. Trans. Met. Chem. 1981, 6, 67. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767. Gree, R. Synthesis 1989, 341. Knölker, H. J. Synlett 1992, 371. Gree, R.; Lellouche, J. P. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1995; Vol. 4, p 129.
21. Franck-Neumann, M. Organametallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 247. Pearson, A. J. Acc. Chem. Res. 1980, 13, 463. Pearson, A. J. Trans. Met. Chem. 1981, 6, 67. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767. Gree, R. Synthesis 1989, 341. Knölker, H. J. Synlett 1992, 371. Gree, R.; Lellouche, J. P. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1995; Vol. 4, p 129.
22. Franck-Neumann, M. Organametallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 247. Pearson, A. J. Acc. Chem. Res. 1980, 13, 463. Pearson, A. J. Trans. Met. Chem. 1981, 6, 67. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767. Gree, R. Synthesis 1989, 341. Knölker, H. J. Synlett 1992, 371. Gree, R.; Lellouche, J. P. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1995; Vol. 4, p 129.
23. Franck-Neumann, M. Organametallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 247. Pearson, A. J. Acc. Chem. Res. 1980, 13, 463. Pearson, A. J. Trans. Met. Chem. 1981, 6, 67. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767. Gree, R. Synthesis 1989, 341. Knölker, H. J. Synlett 1992, 371. Gree, R.; Lellouche, J. P. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1995; Vol. 4, p 129.
24. Franck-Neumann, M. Organametallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 247. Pearson, A. J. Acc. Chem. Res. 1980, 13, 463. Pearson, A. J. Trans. Met. Chem. 1981, 6, 67. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767. Gree, R. Synthesis 1989, 341. Knölker, H. J. Synlett 1992, 371. Gree, R.; Lellouche, J. P. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1995; Vol. 4, p 129.
25. Franck-Neumann, M. Organametallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 247. Pearson, A. J. Acc. Chem. Res. 1980, 13, 463. Pearson, A. J. Trans. Met. Chem. 1981, 6, 67. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767. Gree, R. Synthesis 1989, 341. Knölker, H. J. Synlett 1992, 371. Gree, R.; Lellouche, J. P. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1995; Vol. 4, p 129.
26. Franck-Neumann, M. Organametallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 247. Pearson, A. J. Acc. Chem. Res. 1980, 13, 463. Pearson, A. J. Trans. Met. Chem. 1981, 6, 67. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767. Gree, R. Synthesis 1989, 341. Knölker, H. J. Synlett 1992, 371. Gree, R.; Lellouche, J. P. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1995; Vol. 4, p 129.
27. Clinton, N. A.; Lillya, C. P. J. Am. Chem. Soc. 1970, 92, 3065.
28. Uemura, M.; Minami, T.; Yamashita, Y.; Hiyoshi, K; Hayashi, Y. Tetrahedron Lett. 1987, 28, 641.
29. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
30. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
31. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
32. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
33. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
34. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
35. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
36. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
37. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
38. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
39. For recent examples, see: Donaldson, W. A.; Bell, P. T.; Jin, M.-J. J. Org. Chem. 1992, 441, 449. Donaldson, W. A.; Jin, M.-J. Bull. Soc. Chim. Belg. 1993, 102, 297. Donaldson, W. A.; Jin M.-J.; Bell, P. T. Organometallics 1993, 12, 1174. Donaldson, W. A.; Jin, M.-J. Tetrahedron 1993, 49, 8787. Donaldson W. A.; Shang, L. Tetrahedron Lett. 1995, 36, 1575. Hessler, E.; Schmalz, H. G.; Dürner, G. Tetrahedron Lett. 1994, 35, 4547. Roush, W. R.; Wada, C. K. Tetrahedron Lett. 1994, 35, 7347. Quirosa-Guillou, C.; Lellouche, J. P. J. Org. Chem. 1994, 59, 4693. Gree, D.; Gree R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841. Hachem, A.; Toupet, L.; Gree, R. Tetrahedron Lett. 1995, 36, 1849. Gree, D. M.; Martelli, J. T.; Gree, R. L.; Toupet, L. J. J. Org. Chem. 1995, 60, 2316.
40. Gree, R.; Laabassi, M.; Mosset, P.; Carrie, R. Tetrahedron Lett. 1984, 25, 3693.
41. 19F) of the crude reaction mixtures.
42. The atomic coordinates for this structure have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
43. These reactions have been studied starting with type b and c complexes in racemic form, and thus, these results correspond to diastereoselectivities.
44. Takeuchi, Y.; Kanada, A.; Kawahara, S.; Koizumi, T. J. Org. Chem. 1993, 58, 3483. Abouabdellah, A.; Welch, J. T. Tetrahedron Asymmetry 1994, 5, 1005. Ihara, M.; Kawabuchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron Asymmetry 1994, 5, 1041.
45. Takeuchi, Y.; Kanada, A.; Kawahara, S.; Koizumi, T. J. Org. Chem. 1993, 58, 3483. Abouabdellah, A.; Welch, J. T. Tetrahedron Asymmetry 1994, 5, 1005. Ihara, M.; Kawabuchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron Asymmetry 1994, 5, 1041.
46. Takeuchi, Y.; Kanada, A.; Kawahara, S.; Koizumi, T. J. Org. Chem. 1993, 58, 3483. Abouabdellah, A.; Welch, J. T. Tetrahedron Asymmetry 1994, 5, 1005. Ihara, M.; Kawabuchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron Asymmetry 1994, 5, 1041.
47. Djedaini, F.; Gree, D.; Martelli, J.; Gree, R.; Leroy, L.; Bolard, J.; Toupet, L. Tetrahedron Lett. 1989, 30, 3781.
48. Gree, R.; Laabassi, M.; Mosset, P.; Carrié, R. Tetrahedron Lett. 1985, 26, 2317.
49. Powell, J.; Horvath, M. J. Organometallics 1993, 12, 4073.