Carbanion-Accelerated Vinylcyclopropane Rearrangement. Application in a General, Stereocontrolled Annulation Approach to Cyclopentene Derivatives

Journal of the American Chemical Society

Volumn 107, Issue 15, 1985, Pages 4579-4581

  Danheiser, Rick L ^a   Bronson, Joanne J ^a   Okano, Kazuo ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845378644     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00301a051     Document Type: Article

References (10)

1. Ramaiah, M. Synthesis 1984, 529. (b) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (c) Paquette, L. A. Top. Curr. Chem. 1979, 79, 49.
2. Danheiser, R. L.; Martinez-Davila, C.; Auchus, R. J.; Kadonaga, J. T. J. Am. Chem. Soc. 1981, 103, 2443. (b) Danheiser, R. L.; Martinez-Davila, C.; Morin, J. M. J. Org. Chem. 1980, 45, 1340.
3. For previous examples of carbanion-accelerated pericyclic reactions, see: (a) Comber, R. N.; Swenton, J. S.; Wexler, A. J. J. Am. Chem. Soc. 1979, 101, 5411. (b) Kametani, T.; Tsubuki, M.; Nemoto, H.; Suzuki, K. J. Am. Chem. Soc. 1981, 103, 1256. (c) Cooper, D.; Trippet, S. J. Chem. Soc., Perkin Trans 1 1981, 2127. (d) Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972. (e) Denmark, S. E.; Harmata, M. A. J. Org. Chem. 1983, 48, 3369. (f) Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. (g) Denmark, S. E.; Harmata, M. A. Tetrahedron Lett. 1984, 25, 1543. (h) Blechert, S. Tetrahedron Lett. 1984, 25, 1547.
4. Martel, B.; Hiriat, J. M. Synthesis 1972, 201.
5. Trost, B. M.; Kunz, R. A. J. Org. Chem. 1974, 39, 2648.
6. Tamura, M.; Kochi, J. Synthesis 1971, 303.
7. Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287.
8. 2O as described by: Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Benneche, T.; Undheim, K. Chem. Scr. 1982, 20, 11.
9. Hudlicky, T.; Kutchan, T. M.; Naqui, S. M. Org. React. 1985, 33, 247.
10. For reviews, see: (a) Durst, T. In “Comprehensive Organic Chemistry”; Barton, D., Ollis, W. D. Eds.; Pergamon Press: New York, 1979; pp 171–213. (b) Magnus, P. D. Tetrahedron 1977, 33, 2019.