Synthesis of bis-and oligo-gem-difluorocyclopropanes using the olefin metathesis reaction

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1431-1434

  Itoh, Toshiyuki ^a   Mitsukura, Koichi ^a   Ishida, Nanae ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 0000026174     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000047p     Document Type: Article

References (16)

1. For a review, see: Kitazume, T.; Yamazaki, T. Topics in Current Chemistry; Springer-Verlag: New York, 1997; Vol. 193, pp 91-130.
2. The synthesis of optically active difluorocyclopropane derivatives has recently been reported. (a) Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J-i.; Morikawa, T.; Shiro, M. Tetrahedron; Asymmetry 1994, 5, 1423.
3. (b) Shibuya, A.; Kurishita, M.; Ago, C.; Taguchi, T. Tetrahedron 1996, 52, 271.
4. (c) Shibuya, A.; Sato, A.; Taguchi, T. Bioorg. Med. Chem. Lett. 1998, 8, 1979.
5. (d) Kirihara, M.; Takuwa, T.; Kawasaki, M.; Kakuda, H.; Hirokami, S.-I.; Takahata, H. Chem. Lett. 1999, 405. Biological activities were reported for difluorocyclopropane derivatives.
6. (e) Boger, D. L.; Jenkins, T. J. J. Am. Chem. Soc. 1996, 118, 8860.
7. (f) Taguchi, T.; Kurishita, M.; Shibuya, A.; Aso, K. Tetrahedron 1997, 53, 9497.
8. (g) Csuk, R.; Eversmann, L. Tetrahedron 1998, 54, 6445.
9. (a) Itoh, T.; Mitsukura, K.; Furutani, M. Chem. Lett. 1998, 903.
10. (b) Mitsukura, K.; Korekiyo, S.; Itoh, T. Tetrahedron Lett. 1999, 40, 5739
11. Preliminary results of this project have been reported: Itoh, T.; Mitsukura, K.; Ishida, N. The Nagoya COE-RCMS conference, Jan 6-7, 2000, Nagoya, Japan, P32.
12. MacSpartan Plus was employed for MO (PM3) calculation.
13. For a review see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
14. Recent examples: (a) Scholl, M.; Ding, S.; Lee. C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
15. (b) Ulman, M.; Grubbs, R. H. J. Org. Chem. 1999, 64, 7207.
16. 2 solution. No increase of the chemical yield was observed when the catalyst powder was added to the reaction mixture in a 5-fold portion.