Low-temperature oxyanion-accelerated vinylcyclopropanecyclopentene rearrangement. Reaction of 2-(2-(trimethylsilyl)ethenyl)cyclopropyl acetates with methyl lithium

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3257-3260

  Takeda, Kei ^a   Sakurama, Keiki ^a   Yoshii, Eiichi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030938841     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00579-0     Document Type: Article

References (20)

1. For reviews on vinylcyclopropane-cyclopentene rearrangement, see: Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899-970. Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247-335. Also, see: Wong, H. N. C.; Hon, M-Y.; Tse, C-W.; Yip, Y-C; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198.
2. For reviews on vinylcyclopropane-cyclopentene rearrangement, see: Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899-970. Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247-335. Also, see: Wong, H. N. C.; Hon, M-Y.; Tse, C-W.; Yip, Y-C; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198.
3. For reviews on vinylcyclopropane-cyclopentene rearrangement, see: Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899-970. Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247-335. Also, see: Wong, H. N. C.; Hon, M-Y.; Tse, C-W.; Yip, Y-C; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198.
4. (a) Danheiser, R. L.; Martinez-Davila, C.; Morin, Jr., J. M. J. Org. Chem. 1980, 45, 1340-1341.
5. (b) Danheiser, R. L.; Martinez-Davila, C.; Auchus, R. J.; Kadonaga, J. T. J. Am. Chem. Soc. 1981, 103, 2443-2446. For a carbanion-accelerated version, see: Danheiser, R. L.; Bronson, J. J.; Okano, K. J Am. Chem. Soc. 1985, 107, 4579-4581.
6. (b) Danheiser, R. L.; Martinez-Davila, C.; Auchus, R. J.; Kadonaga, J. T. J. Am. Chem. Soc. 1981, 103, 2443-2446. For a carbanion-accelerated version, see: Danheiser, R. L.; Bronson, J. J.; Okano, K. J Am. Chem. Soc. 1985, 107, 4579-4581.
7. For a review of charge accelerated rearrangement, see: (a) Bronson, J. J.; Danheiser, R. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 999-1036.
8. (b) Wilson, S. R. Org. React. 1993, 43, 93-250.
9. Takeda, K.; Fujisawa, M.; Makino, T.; Yoshii, E.; Yamaguchi, K. J. Am. Chem. Soc. 1993, 115, 9351-9352.
10. Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949-960.
11. Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609-5617.
12. Murray, C. K.; Yang, D. C. Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 5660-5662.
13. For reviews on the synthetic applications of Fischer carbene complexes, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1065-1113.
14. (b) Wulff, W. D. In Advances in Metal-Organic Chemistry; Libeskind, L. S., Ed.; JAI Press Inc.; Greenwich, CT, 1989; Vol. 1, pp 209-393.
15. (c) Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587-608.
16. 4
17. The E/Z ratios were variable although the E isomer always predominated, and were independent of the ratios of 8 and 9.
18. No E/Z and syn/anti isomerization was observed in a small amount of 7 recovered from the reaction mixture.
19. Attempted trapping of 10 as an acetate with acetyl bromide and isolation of the corresponding vinylcy-clopropanol by nonaqueous workup were unsuccessful.
20. Takeda, K.; Nakatani, J.; Nakamura, H.; Sako, K.; Yoshii, E.; Yamaguchi, K. Synlett 1993, 841-843.