Synthesis of 2,5-diaryl-3-halofurans via regioselective ring cleavage of aryl 3-aryl-2,2-dihalocyclopropyl ketones

Synthesis

Volumn , Issue 3, 1996, Pages 388-392

  Tanabe, Yoo ^a   Wakimura, Ken Ichi ^a   Nishii, Yoshinori ^a   Muroya, Yukari ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

gem dihalocyclopropane; halofuran; lithiation; regioselective; tetrasubsti tuted furan

Indexed keywords

CYCLOPROPANE DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030000571     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4218     Document Type: Article

References (23)

1. Wong, H. N. C.; Hon, M-Y.; Tse, C-W; Yip, Y-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. Reißig, U.-H. Top. Curr. Chem. 1988, 144, 73. Saigo, K.; Shimada, S.; Hashimoto, Y. Chem. Lett. 1990, 1101. Ejiri, S.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 8707. Iwasawa, N. Chem. Lett. 1992, 473.
2. Wong, H. N. C.; Hon, M-Y.; Tse, C-W; Yip, Y-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. Reißig, U.-H. Top. Curr. Chem. 1988, 144, 73. Saigo, K.; Shimada, S.; Hashimoto, Y. Chem. Lett. 1990, 1101. Ejiri, S.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 8707. Iwasawa, N. Chem. Lett. 1992, 473.
3. Wong, H. N. C.; Hon, M-Y.; Tse, C-W; Yip, Y-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. Reißig, U.-H. Top. Curr. Chem. 1988, 144, 73. Saigo, K.; Shimada, S.; Hashimoto, Y. Chem. Lett. 1990, 1101. Ejiri, S.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 8707. Iwasawa, N. Chem. Lett. 1992, 473.
4. Wong, H. N. C.; Hon, M-Y.; Tse, C-W; Yip, Y-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. Reißig, U.-H. Top. Curr. Chem. 1988, 144, 73. Saigo, K.; Shimada, S.; Hashimoto, Y. Chem. Lett. 1990, 1101. Ejiri, S.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 8707. Iwasawa, N. Chem. Lett. 1992, 473.
5. Wong, H. N. C.; Hon, M-Y.; Tse, C-W; Yip, Y-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. Reißig, U.-H. Top. Curr. Chem. 1988, 144, 73. Saigo, K.; Shimada, S.; Hashimoto, Y. Chem. Lett. 1990, 1101. Ejiri, S.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 8707. Iwasawa, N. Chem. Lett. 1992, 473.
6. Paham, W. E.; Schweizer, E. E. Organic Reactions, Wiley, New York, 1963, Vol. 13; p. 55. Starks, C. M.; Liotta, C. Phase Transfer Catalysis, Academic Press, 1978, p. 224. Makosza, M.; Wawrzyniewicz, M. Tetrahedron Lett. 1969, 4659.
7. Paham, W. E.; Schweizer, E. E. Organic Reactions, Wiley, New York, 1963, Vol. 13; p. 55. Starks, C. M.; Liotta, C. Phase Transfer Catalysis, Academic Press, 1978, p. 224. Makosza, M.; Wawrzyniewicz, M. Tetrahedron Lett. 1969, 4659.
8. Paham, W. E.; Schweizer, E. E. Organic Reactions, Wiley, New York, 1963, Vol. 13; p. 55. Starks, C. M.; Liotta, C. Phase Transfer Catalysis, Academic Press, 1978, p. 224. Makosza, M.; Wawrzyniewicz, M. Tetrahedron Lett. 1969, 4659.
9. Seyferth, D.; Yamazaki, H.; Alleston, D. L. J. Org. Chem. 1963, 28, 703. Osuka, A.; Takeuchi, K.; Suzuki, H. Bull. Chem. Soc. Jpn. 1984, 57, 303. Miura, K.; Ichinose, Y.; Fugami, K.; Oshima, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143 and references cited therein.
10. Seyferth, D.; Yamazaki, H.; Alleston, D. L. J. Org. Chem. 1963, 28, 703. Osuka, A.; Takeuchi, K.; Suzuki, H. Bull. Chem. Soc. Jpn. 1984, 57, 303. Miura, K.; Ichinose, Y.; Fugami, K.; Oshima, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143 and references cited therein.
11. Seyferth, D.; Yamazaki, H.; Alleston, D. L. J. Org. Chem. 1963, 28, 703. Osuka, A.; Takeuchi, K.; Suzuki, H. Bull. Chem. Soc. Jpn. 1984, 57, 303. Miura, K.; Ichinose, Y.; Fugami, K.; Oshima, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143 and references cited therein.
12. Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1977, 2347. Holm, K. H.; Skattebøl, L. J. Am. Chem. Soc. 1977, 99, 5480. S-Rouvier, C. Tetrahedron 1981, 37, 4195. DeWeese, F. T.; Minter, D. E.; Nosovitch, J. T.; Rudel, M. G. Tetrahedron 1986, 42, 4195. Holm, K. H.; Mohamed, E. A.; Skattebøl, L. Acta Chem. Scand. 1993, 47, 500.
13. Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1977, 2347. Holm, K. H.; Skattebøl, L. J. Am. Chem. Soc. 1977, 99, 5480. S-Rouvier, C. Tetrahedron 1981, 37, 4195. DeWeese, F. T.; Minter, D. E.; Nosovitch, J. T.; Rudel, M. G. Tetrahedron 1986, 42, 4195. Holm, K. H.; Mohamed, E. A.; Skattebøl, L. Acta Chem. Scand. 1993, 47, 500.
14. Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1977, 2347. Holm, K. H.; Skattebøl, L. J. Am. Chem. Soc. 1977, 99, 5480. S-Rouvier, C. Tetrahedron 1981, 37, 4195. DeWeese, F. T.; Minter, D. E.; Nosovitch, J. T.; Rudel, M. G. Tetrahedron 1986, 42, 4195. Holm, K. H.; Mohamed, E. A.; Skattebøl, L. Acta Chem. Scand. 1993, 47, 500.
15. Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1977, 2347. Holm, K. H.; Skattebøl, L. J. Am. Chem. Soc. 1977, 99, 5480. S-Rouvier, C. Tetrahedron 1981, 37, 4195. DeWeese, F. T.; Minter, D. E.; Nosovitch, J. T.; Rudel, M. G. Tetrahedron 1986, 42, 4195. Holm, K. H.; Mohamed, E. A.; Skattebøl, L. Acta Chem. Scand. 1993, 47, 500.
16. Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1977, 2347. Holm, K. H.; Skattebøl, L. J. Am. Chem. Soc. 1977, 99, 5480. S-Rouvier, C. Tetrahedron 1981, 37, 4195. DeWeese, F. T.; Minter, D. E.; Nosovitch, J. T.; Rudel, M. G. Tetrahedron 1986, 42, 4195. Holm, K. H.; Mohamed, E. A.; Skattebøl, L. Acta Chem. Scand. 1993, 47, 500.
17. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. J. Org. Chem. 1993, 58, 2958.
18. Seko, S.; Tanabe, Y.; Suzukamo, G. Tetrahedron Lett. 1990, 31, 6883. Nishii, Y.; Tanabe, Y. Tetrahedron Lett. 1995, 36, 8803. Nishii, Y.; Matsumura, H.; Muroya, Y.; Tsuchiya, T; Tanabe, Y. Biosci. Biotech. Biochem. 1995, 59, 1355.
19. Seko, S.; Tanabe, Y.; Suzukamo, G. Tetrahedron Lett. 1990, 31, 6883. Nishii, Y.; Tanabe, Y. Tetrahedron Lett. 1995, 36, 8803. Nishii, Y.; Matsumura, H.; Muroya, Y.; Tsuchiya, T; Tanabe, Y. Biosci. Biotech. Biochem. 1995, 59, 1355.
20. Seko, S.; Tanabe, Y.; Suzukamo, G. Tetrahedron Lett. 1990, 31, 6883. Nishii, Y.; Tanabe, Y. Tetrahedron Lett. 1995, 36, 8803. Nishii, Y.; Matsumura, H.; Muroya, Y.; Tsuchiya, T; Tanabe, Y. Biosci. Biotech. Biochem. 1995, 59, 1355.
21. Tanabe, Y.; Nishii, Y.; Wakimura, K. Chem. Lett. 1994, 1757.
22. Murphy, W. S.; Wattanasin, S. J. Chem. Soc., Perkin Trans. 1 1981, 2920; J. Chem. Soc., Chem. Commun. 1980, 262.
23. Murphy, W. S.; Wattanasin, S. J. Chem. Soc., Perkin Trans. 1 1981, 2920; J. Chem. Soc., Chem. Commun. 1980, 262.