Regioselective nucleophilic additions to cross-conjugated dienone system bearing β-fluorine: A versatile approach to highly substituted 2-cyclopentenones

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2345-2348

  Ichikawa, Junji ^a   Fujiwara, Masaki ^a   Miyazaki, Shinji ^b   Ikemoto, Masahiro ^b   Okauchi, Tatsuo ^b   Minami, Toru ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; FLUORINATED HYDROCARBON;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CYCLOPENTANES; HYDROCARBONS, FLUORINATED; STEREOISOMERISM;

EID: 0035954897     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0161458     Document Type: Article

References (37)

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16. Paleta, O.; Pelter, A.; Kebrle, J. Tetrahedron Lett. 1994, 35, 9259 and references therein. Tellier, F.; Sauvêtre, R. J. Fluorine Chem. 1996, 76, 181. Burdon, J.; Coe, P. L.; Haslock, I. b.; Powell, R. L. Chem. Commun. 1996, 49 and references therein. See also: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743. For 1,3-carbonyl transposition, see: Larock, R. C. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd ed.; VCH Publishers: New York, 1999; p 1201.
17. Paleta, O.; Pelter, A.; Kebrle, J. Tetrahedron Lett. 1994, 35, 9259 and references therein. Tellier, F.; Sauvêtre, R. J. Fluorine Chem. 1996, 76, 181. Burdon, J.; Coe, P. L.; Haslock, I. b.; Powell, R. L. Chem. Commun. 1996, 49 and references therein. See also: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743. For 1,3-carbonyl transposition, see: Larock, R. C. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd ed.; VCH Publishers: New York, 1999; p 1201.
18. For recent reports on the synthesis of alkylidene cyclopentenones, see: Herndon, J. W.; Zhu, J.; Sampedro, D. Tetrahedron 2000, 56, 4985 and references therein. Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491 and references therein.
19. For recent reports on the synthesis of alkylidene cyclopentenones, see: Herndon, J. W.; Zhu, J.; Sampedro, D. Tetrahedron 2000, 56, 4985 and references therein. Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491 and references therein.
20. Chambers, R. D. Fluorine in Organic Chemistry; Antony Rowe: Chippenham, 1973; p 1. Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Ed.; Plenum Press: New York, 1994; p 57. Allen, A. D.; Tidwell, T. T. In Advances in Carbocation Chemistry; Creary, X., Ed.; Jai Press: Greenwich, 1989; Vol. 1, p 1.
21. Chambers, R. D. Fluorine in Organic Chemistry; Antony Rowe: Chippenham, 1973; p 1. Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Ed.; Plenum Press: New York, 1994; p 57. Allen, A. D.; Tidwell, T. T. In Advances in Carbocation Chemistry; Creary, X., Ed.; Jai Press: Greenwich, 1989; Vol. 1, p 1.
22. Chambers, R. D. Fluorine in Organic Chemistry; Antony Rowe: Chippenham, 1973; p 1. Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Ed.; Plenum Press: New York, 1994; p 57. Allen, A. D.; Tidwell, T. T. In Advances in Carbocation Chemistry; Creary, X., Ed.; Jai Press: Greenwich, 1989; Vol. 1, p 1.
23. For reports on cationic cyclizations where fluorine acts as an α-cation-stabilizing substituent, see: Johnson, W. S.; Daub, G. W.; Lyle, T. A.; Niwa, M. J. Am. Chem. Soc. 1980, 102, 7800. Johnson, W. S.; Lyle, T. A.; Daub, G. W. J. Org. Chem. 1982, 47, 161. Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150 and references therein. Morikawa, T.; Kumadaki, I.; Shiro, M. Chem. Pharm. Bull. 1985, 33, 5144.
24. For reports on cationic cyclizations where fluorine acts as an α-cation-stabilizing substituent, see: Johnson, W. S.; Daub, G. W.; Lyle, T. A.; Niwa, M. J. Am. Chem. Soc. 1980, 102, 7800. Johnson, W. S.; Lyle, T. A.; Daub, G. W. J. Org. Chem. 1982, 47, 161. Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150 and references therein. Morikawa, T.; Kumadaki, I.; Shiro, M. Chem. Pharm. Bull. 1985, 33, 5144.
25. For reports on cationic cyclizations where fluorine acts as an α-cation-stabilizing substituent, see: Johnson, W. S.; Daub, G. W.; Lyle, T. A.; Niwa, M. J. Am. Chem. Soc. 1980, 102, 7800. Johnson, W. S.; Lyle, T. A.; Daub, G. W. J. Org. Chem. 1982, 47, 161. Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150 and references therein. Morikawa, T.; Kumadaki, I.; Shiro, M. Chem. Pharm. Bull. 1985, 33, 5144.
26. For reports on cationic cyclizations where fluorine acts as an α-cation-stabilizing substituent, see: Johnson, W. S.; Daub, G. W.; Lyle, T. A.; Niwa, M. J. Am. Chem. Soc. 1980, 102, 7800. Johnson, W. S.; Lyle, T. A.; Daub, G. W. J. Org. Chem. 1982, 47, 161. Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150 and references therein. Morikawa, T.; Kumadaki, I.; Shiro, M. Chem. Pharm. Bull. 1985, 33, 5144.
27. Crimmins, M. T.; Dedopoulou, D. Synth. Commun. 1992, 22, 1953.
28. For a review of organocopper reagents, see: Lipshutz, B. H. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; John Wiley & Sons: Chichester, 1994; p 283.
29. We have reported that the fluorines on the β-carbon of α,β-unsaturated ketones are easily replaced by carbon and heteroatom nucleophiles via an addition - elimination process, see: Ichikawa, J., Yokota, Y.; Kobayashi, M.; Minami, T. Synlett 1993, 186. Ichikawa, J.; Kobayashi, M.; Yokota, Y.; Noda, Y.; Minami, T. Tetrahedron 1994, 50, 11637. Ichikawa, J.; Yokota, Y.; Kobayashi, M.; Amano, K.; Minami, T. Synlett 1996, 243. Ichikawa, J.; Kobayashi, M.; Noda, Y.; Yokota, N.; Amano, K.; Minami, T. J. Org. Chem. 1996, 61, 2763. See also: Xiao, L.; Kitazume, T. J. Fluorine Chem. 1997, 86, 99.
30. We have reported that the fluorines on the β-carbon of α,β-unsaturated ketones are easily replaced by carbon and heteroatom nucleophiles via an addition - elimination process, see: Ichikawa, J., Yokota, Y.; Kobayashi, M.; Minami, T. Synlett 1993, 186. Ichikawa, J.; Kobayashi, M.; Yokota, Y.; Noda, Y.; Minami, T. Tetrahedron 1994, 50, 11637. Ichikawa, J.; Yokota, Y.; Kobayashi, M.; Amano, K.; Minami, T. Synlett 1996, 243. Ichikawa, J.; Kobayashi, M.; Noda, Y.; Yokota, N.; Amano, K.; Minami, T. J. Org. Chem. 1996, 61, 2763. See also: Xiao, L.; Kitazume, T. J. Fluorine Chem. 1997, 86, 99.
31. We have reported that the fluorines on the β-carbon of α,β-unsaturated ketones are easily replaced by carbon and heteroatom nucleophiles via an addition - elimination process, see: Ichikawa, J., Yokota, Y.; Kobayashi, M.; Minami, T. Synlett 1993, 186. Ichikawa, J.; Kobayashi, M.; Yokota, Y.; Noda, Y.; Minami, T. Tetrahedron 1994, 50, 11637. Ichikawa, J.; Yokota, Y.; Kobayashi, M.; Amano, K.; Minami, T. Synlett 1996, 243. Ichikawa, J.; Kobayashi, M.; Noda, Y.; Yokota, N.; Amano, K.; Minami, T. J. Org. Chem. 1996, 61, 2763. See also: Xiao, L.; Kitazume, T. J. Fluorine Chem. 1997, 86, 99.
32. We have reported that the fluorines on the β-carbon of α,β-unsaturated ketones are easily replaced by carbon and heteroatom nucleophiles via an addition - elimination process, see: Ichikawa, J., Yokota, Y.; Kobayashi, M.; Minami, T. Synlett 1993, 186. Ichikawa, J.; Kobayashi, M.; Yokota, Y.; Noda, Y.; Minami, T. Tetrahedron 1994, 50, 11637. Ichikawa, J.; Yokota, Y.; Kobayashi, M.; Amano, K.; Minami, T. Synlett 1996, 243. Ichikawa, J.; Kobayashi, M.; Noda, Y.; Yokota, N.; Amano, K.; Minami, T. J. Org. Chem. 1996, 61, 2763. See also: Xiao, L.; Kitazume, T. J. Fluorine Chem. 1997, 86, 99.
33. We have reported that the fluorines on the β-carbon of α,β-unsaturated ketones are easily replaced by carbon and heteroatom nucleophiles via an addition - elimination process, see: Ichikawa, J., Yokota, Y.; Kobayashi, M.; Minami, T. Synlett 1993, 186. Ichikawa, J.; Kobayashi, M.; Yokota, Y.; Noda, Y.; Minami, T. Tetrahedron 1994, 50, 11637. Ichikawa, J.; Yokota, Y.; Kobayashi, M.; Amano, K.; Minami, T. Synlett 1996, 243. Ichikawa, J.; Kobayashi, M.; Noda, Y.; Yokota, N.; Amano, K.; Minami, T. J. Org. Chem. 1996, 61, 2763. See also: Xiao, L.; Kitazume, T. J. Fluorine Chem. 1997, 86, 99.
34. Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519. For recent reports on ATPH, see: Saito, S.; Sone, T.; Murase, M.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10216. Ooi, T.; Hokke, Y.; Tayama, E.; Maruoka, K. Tetrahedron 2001, 57, 135 and references therein.
35. Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519. For recent reports on ATPH, see: Saito, S.; Sone, T.; Murase, M.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10216. Ooi, T.; Hokke, Y.; Tayama, E.; Maruoka, K. Tetrahedron 2001, 57, 135 and references therein.
36. Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519. For recent reports on ATPH, see: Saito, S.; Sone, T.; Murase, M.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10216. Ooi, T.; Hokke, Y.; Tayama, E.; Maruoka, K. Tetrahedron 2001, 57, 135 and references therein.
37. 6).