Diastereoselectivity Control in the Zirconocene-Mediated Ring Contraction of 4-Vinylfuranosides to Enantiopure Multiply Functionalized Cyclobutanes

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1927-1929

  Paquette, Leo A ^a   Cunière, Nicolas ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ARABINOSE; CYCLOBUTANE DERIVATIVE; FURAN DERIVATIVE; ORGANOMETALLIC COMPOUND; ZIRCONIUM; ZIRCONOCENE DICHLORIDE;

ARTICLE; CHEMISTRY; ISOLATION AND PURIFICATION; STEREOISOMERISM;

ANTINEOPLASTIC AGENTS; ARABINOSE; CYCLOBUTANES; FURANS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZIRCONIUM;

EID: 0037198757     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020063h     Document Type: Article

References (22)

1. (a) Robertson, J. M.; Todd, G. Chem. Ind. (London) 1953, 437; J. Chem. Soc. 1955, 1254.
2. (a) Robertson, J. M.; Todd, G. Chem. Ind. (London) 1953, 437; J. Chem. Soc. 1955, 1254.
3. (b) Corey, E J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1964, 86, 485.
4. (a) Kepler, J. A.; Wall, M. E.; Mason, J. E.; Basset, C.; McPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1967, 89, 1260.
5. (b) Cane, D. E.; Nachbar, R. B.; Clardy, J.; Finer, J. Tetrahedron Lett. 1977, 4277.
6. (c) Semmelhack, M. F.; Tomoda, S.; Nagaoka, H.; Boettger, S. D.; Hurst, K. M. J. Am. Chem. Soc. 1982, 104, 747.
7. (a) Pulici M.; Sugawara, F.; Koshino, H.; Uzawa, J.; Yoshida, S.; Lobkovsky, E.; Clardy, J. J. Org.Chem. 1996, 61, 2122.
8. (b) Johnston D.; Francon, N.; Edmonds, D. J.; Procter, D. J. Org. Lett. 2001, 3, 2001.
9. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
10. (a) Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 1295.
11. (b) Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 7873.
12. (c) Ito, H.; Nakamura, T.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 3769.
13. (d) Ito, H.; Taguchi, T.; Hanzawa, Y. J. Org. Chem. 1993, 58, 774.
14. (e) Rousset, C. J.; Swanson, D. R.; Lamaty, F.; Negishi, E. Tetrahedron Lett. 1989, 30, 5105.
15. (a) Ito, H.; Motoki, Y.; Taguchi, T.; Hanzawa, Y. J. Am. Chem. Soc. 1993, 115, 8835.
16. (b) Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299.
17. Aurrecoechea, J. M.; López, B.; Arrate, M. J. Org. Chem. 2000, 65, 6493.
18. (a) Copland, C.; Stick, R. V. Aust. J. Chem. 1977, 30, 1269.
19. (b) Weygand, F.; Wolf, H. Chem. Ber. 1952, 85, 256.
20. (c) Jones, J. K. N.; Thompson, J. L. Can. J. Chem. 1957, 35, 955.
21. Dahlman, O.; Garegg, P. J.; Mayer, H.; Schramek, S. Acta Chem. Scand. B 1986, 40, 15.
22. Otmar, M.; Rosenberg, I.; Masojidkova, M.; Holy, A. Collect. Czech. Chem. Commun. 1993, 58, 2180.