Highly efficient and stereoselective access to (Z)-α,β- difluoroallyl alcohols and (Z)-α-fluoro-α,β-unsaturated aldehydes based on the reaction of 2,3,3-trifluoro-1-propenyl p- chlorobenzenesulfonate with Grignard reagents

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1913-1916

  Funabiki, Kazumasa ^a   Fukushima, Yoshitaka ^a   Inagaki, Tomomi ^a   Murata, Eiji ^a   Matsui, Masaki ^a   Shibata, Katsuyoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; PROPANOL;

ARTICLE; CATALYSIS; DRUG CONFORMATION; DRUG HYDROLYSIS; DRUG SYNTHESIS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0032473859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00046-X     Document Type: Article

References (41)

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9. 5. For recent reports, see: Bégué, J. -P.; Bonnet-Delpon, D.; Percy, J. M.; Rock, M. H.; Wilkes, R. D. J. Chem. Soc., Chem. Commun. 1995, 1857. Bégué, J. -P.; Bonnet-Delpon, D.; Rock, M. H. Tetrahedron Lett. 1994, 35, 6097-6100. Lee, J.; Tsukazaki, M.; Snieckus, V. Tetrahedron Lett. 1993, 34, 415-418. Bennett, A. J.; Percy, J. M.; Rock, M. H. Synlett 1992, 483-484. Percy, J. M. Tetrahedron Lett. 1990, 31, 3931-3932.
10. 5. For recent reports, see: Bégué, J. -P.; Bonnet-Delpon, D.; Percy, J. M.; Rock, M. H.; Wilkes, R. D. J. Chem. Soc., Chem. Commun. 1995, 1857. Bégué, J. -P.; Bonnet-Delpon, D.; Rock, M. H. Tetrahedron Lett. 1994, 35, 6097-6100. Lee, J.; Tsukazaki, M.; Snieckus, V. Tetrahedron Lett. 1993, 34, 415-418. Bennett, A. J.; Percy, J. M.; Rock, M. H. Synlett 1992, 483-484. Percy, J. M. Tetrahedron Lett. 1990, 31, 3931-3932.
11. 5. For recent reports, see: Bégué, J. -P.; Bonnet-Delpon, D.; Percy, J. M.; Rock, M. H.; Wilkes, R. D. J. Chem. Soc., Chem. Commun. 1995, 1857. Bégué, J. -P.; Bonnet-Delpon, D.; Rock, M. H. Tetrahedron Lett. 1994, 35, 6097-6100. Lee, J.; Tsukazaki, M.; Snieckus, V. Tetrahedron Lett. 1993, 34, 415-418. Bennett, A. J.; Percy, J. M.; Rock, M. H. Synlett 1992, 483-484. Percy, J. M. Tetrahedron Lett. 1990, 31, 3931-3932.
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23. 4 was usually employed, see: Ref. 6a,b. Very recently, iodine-catalyzed allylic rearrangement of fluoroallyl alcohols was reported, see: Tellier, F.; Sauvére, R. Tetrahedron Lett. 1995, 36, 4223-4226. Dubuffet, T.; Bidon, C.; Martinet, P.; Sauvére, R.; Normant, J. -F. J. Organomet. Chem. 1990, 393, 161-172.
24. 4 was usually employed, see: Ref. 6a,b. Very recently, iodine-catalyzed allylic rearrangement of fluoroallyl alcohols was reported, see: Tellier, F.; Sauvére, R. Tetrahedron Lett. 1995, 36, 4223-4226. Dubuffet, T.; Bidon, C.; Martinet, P.; Sauvére, R.; Normant, J. -F. J. Organomet. Chem. 1990, 393, 161-172.
25. 10. Our contribution to α-fluoro-β-alkyl or aryl-α,β-unsaturated aldehydes, see: Ref. 7b. For other reports, see. Ref. 6b. Satoh, T.; Kitoh, Y; Onda, K.; Takano, K.; Yamakawa, K. Tetrahedron 1994, 50, 4957-4972. Patrick, T. B.; Hosseini, S.; Banis, S. Tetrahedron Lett. 1990, 37, 179-182. Bessiere, Y.; Savary, D. N. -H.; Schlosser, M. Helv. Chim. Acta 1977, 60, 1739-1746. Kimoto, H.; Muramatsu, H.; Inukai, K. Nippon Kagaku Kaishi, 1975, 1926-1933.
26. 10. Our contribution to α-fluoro-β-alkyl or aryl-α,β-unsaturated aldehydes, see: Ref. 7b. For other reports, see. Ref. 6b. Satoh, T.; Kitoh, Y; Onda, K.; Takano, K.; Yamakawa, K. Tetrahedron 1994, 50, 4957-4972. Patrick, T. B.; Hosseini, S.; Banis, S. Tetrahedron Lett. 1990, 37, 179-182. Bessiere, Y.; Savary, D. N. -H.; Schlosser, M. Helv. Chim. Acta 1977, 60, 1739-1746. Kimoto, H.; Muramatsu, H.; Inukai, K. Nippon Kagaku Kaishi, 1975, 1926-1933.
27. 10. Our contribution to α-fluoro-β-alkyl or aryl-α,β-unsaturated aldehydes, see: Ref. 7b. For other reports, see. Ref. 6b. Satoh, T.; Kitoh, Y; Onda, K.; Takano, K.; Yamakawa, K. Tetrahedron 1994, 50, 4957-4972. Patrick, T. B.; Hosseini, S.; Banis, S. Tetrahedron Lett. 1990, 37, 179-182. Bessiere, Y.; Savary, D. N. -H.; Schlosser, M. Helv. Chim. Acta 1977, 60, 1739-1746. Kimoto, H.; Muramatsu, H.; Inukai, K. Nippon Kagaku Kaishi, 1975, 1926-1933.
28. 10. Our contribution to α-fluoro-β-alkyl or aryl-α,β-unsaturated aldehydes, see: Ref. 7b. For other reports, see. Ref. 6b. Satoh, T.; Kitoh, Y; Onda, K.; Takano, K.; Yamakawa, K. Tetrahedron 1994, 50, 4957-4972. Patrick, T. B.; Hosseini, S.; Banis, S. Tetrahedron Lett. 1990, 37, 179-182. Bessiere, Y.; Savary, D. N. -H.; Schlosser, M. Helv. Chim. Acta 1977, 60, 1739-1746. Kimoto, H.; Muramatsu, H.; Inukai, K. Nippon Kagaku Kaishi, 1975, 1926-1933.
29. 2O: M, 170.0543.
30. 3CuLi resulted in the decomposition of 1.
31. 13. For the similar generation of polyfluoroalkyl ketone enolate, see: Doussot, P.; Portella, C. J. Org. Chem. 1993, 58, 6675-6680. Ishihara, T.; Kuroboshi, M.; Yamaguchi, K.; Okada, Y. J. Org. Chem. 1990, 55, 3107-3114.
32. 13. For the similar generation of polyfluoroalkyl ketone enolate, see: Doussot, P.; Portella, C. J. Org. Chem. 1993, 58, 6675-6680. Ishihara, T.; Kuroboshi, M.; Yamaguchi, K.; Okada, Y. J. Org. Chem. 1990, 55, 3107-3114.
33. 14. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087. Amos, R. D.; Handy, N. C.; Jones, P. G. A.; Kirby, J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans. 2 1992, 549-558. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1988, 92, 2729-2733. Dixon, D. A.; Matsuzawa, N.; Walker, S. C. J. Phys. Chem. 1992, 96, 10740-1C746. For recent reviews, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. 1996, 54, 665-674. O' Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
34. 14. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087. Amos, R. D.; Handy, N. C.; Jones, P. G. A.; Kirby, J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans. 2 1992, 549-558. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1988, 92, 2729-2733. Dixon, D. A.; Matsuzawa, N.; Walker, S. C. J. Phys. Chem. 1992, 96, 10740-1C746. For recent reviews, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. 1996, 54, 665-674. O' Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
35. 14. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087. Amos, R. D.; Handy, N. C.; Jones, P. G. A.; Kirby, J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans. 2 1992, 549-558. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1988, 92, 2729-2733. Dixon, D. A.; Matsuzawa, N.; Walker, S. C. J. Phys. Chem. 1992, 96, 10740-1C746. For recent reviews, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. 1996, 54, 665-674. O' Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
36. 14. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087. Amos, R. D.; Handy, N. C.; Jones, P. G. A.; Kirby, J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans. 2 1992, 549-558. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1988, 92, 2729-2733. Dixon, D. A.; Matsuzawa, N.; Walker, S. C. J. Phys. Chem. 1992, 96, 10740-1C746. For recent reviews, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. 1996, 54, 665-674. O' Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
37. 14. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087. Amos, R. D.; Handy, N. C.; Jones, P. G. A.; Kirby, J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans. 2 1992, 549-558. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1988, 92, 2729-2733. Dixon, D. A.; Matsuzawa, N.; Walker, S. C. J. Phys. Chem. 1992, 96, 10740-1C746. For recent reviews, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. 1996, 54, 665-674. O' Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
38. 14. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087. Amos, R. D.; Handy, N. C.; Jones, P. G. A.; Kirby, J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans. 2 1992, 549-558. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1988, 92, 2729-2733. Dixon, D. A.; Matsuzawa, N.; Walker, S. C. J. Phys. Chem. 1992, 96, 10740-1C746. For recent reviews, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. 1996, 54, 665-674. O' Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
39. 15. For reports on the stereoselective synthesis of organofluorine molecules utilizing the σ* orbital associated with a fluorine or trifluoromethyl group, see: Yamazaki, T.; Shinohara, N.; Kitazume, T.; Sato, S. J. Org. Chem. 1995, 60, 8140-8141. Bridge, C. F.; O'Hagan, D.; Reynolds, K. A.; Wallace, K. K. J. Chem. Soc., Chem. Commun. 1995, 2329-2330.
40. 15. For reports on the stereoselective synthesis of organofluorine molecules utilizing the σ* orbital associated with a fluorine or trifluoromethyl group, see: Yamazaki, T.; Shinohara, N.; Kitazume, T.; Sato, S. J. Org. Chem. 1995, 60, 8140-8141. Bridge, C. F.; O'Hagan, D.; Reynolds, K. A.; Wallace, K. K. J. Chem. Soc., Chem. Commun. 1995, 2329-2330.
41. 16. Detailed results of M K10 catalyzed hydrolysis of 2 will be reported elsewhere.