Synthesis of 4-Hetero-Substituted Pyranosides via Dioxenium Cation-Olefin Cyclization

Journal of Organic Chemistry

Volumn 52, Issue 18, 1987, Pages 4128-4130

  Perron, Francoise ^a   Albizati, Kim F ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001162607     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00227a037     Document Type: Article

References (16)

1. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapters 5 and 6.
2. Winstead, R. C.; Simpson, T. H.; Lock, G. A.; Schiavelli, M. D.; Thompson, D. W. J. Org. Chem. 1986,51, 275.
3. Johnson, W. S.; Chen, Y. G. ; Kellogg, M. S. J. Am. Chem. Soc. 1983, 105, 6653.
4. Overman, L. E.; Blumenkopf, T. A. Chem. Rev. 1986, 86, 857.
5. Also see: Nussbaumer, C.; Frater, G. Helv. Chim. Acta 1987, 70, 396.
6. Mander, L. N.; Mundill, P. H. C. Synthesis 1981, 620. Oikawa, Y.; Yonemitsu, O. Tetrahedron 1974. 30. 2653.
7. Andersen, N. H.; Yamamoto, Y.; Denniston, A. D. Tetrahedron Lett. 1975, 4547. Rigby, J. A.; Kotnis, A.; Kramer, J. B. Synthesis 1983, 2939.
8. Schoemaker, H. E.; Dijkink, J.; Speckamp, W. N. Tetrahedron 1978, 34, 163.
9. To our knowledge, only one previous example of this process has been described, in which the cyclization occurred onto an enol ether. See: Kocienski, P.; Street, S. D. A. J. Chem. Soc., Chem. Commun. 1984, 571.
10. Albers-Schonberg, G.; Arison, B. H.; Chabala, J. C.; Douglas, A. W.; Eskola, P.; Fisher, M. H.; Lusi, A.; Mrozik, H.; Smith, J. L.; Tolman, R. L. J. Am. Chem. Soc. 1981, 103, 4216.
11. Moore, R. E.; Blackman, A. J.; Cheuk, C. E.; Mynderse, J.; Matsumoto, G.; Clardy, J.; Woodard, R. W.; Craig, J. C. J. Org. Chem. 1984, 49, 2484. Moore, R. E.; Mynderse, J. J. Am. Chem. Soc. 1978, 43, 2301.
12. Spector, I.; Shochet, N. R.; Kashman, Y.; Groweiss, A. Science (Washington, D. C.) 1983, 219, 493.
13. Lynn, D. G.; Phillips, N. J.; Hutton, W. C.; Shabanowitz, J.; Fennell, D. E. J. Am. Chem. Soc. 1982, 104, 7319.
14. Barchi, J. J.; Moore, R. E.; Patterson, G. L. M. J. Am. Chem. Soc. 1984, 106, 8193.
15. Crews, P.; Naylor, S.; Hanke, F. J.; Hogue, E. R.; Kho, E.; Braslau, R. J. Org. Chem. 1984, 49, 1371. Stevens, R. V.; Albizati, K. F. J. Org. Chem. 1985, 50, 632.
16. Although generally considered a ground-state phenomenon, the anomeric effect might be manifested in a reaction involving a late transition state (in this case a kinetic effect), such as one involving a highly stabilized cation. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: New York, 1983.