Facile preparation of perfluoro-tert-butyl ethers by the Mitsunobu reaction

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 361-362

  Sebesta, David P ^a   O'Rourke, Sarah S ^a   Pieken, Wolfgang A ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001066695     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951515p     Document Type: Article

References (14)

1. (a) Tuerk, C.; Gold, L. Science 1990, 249, 505-510.
2. (b) Lin, Y.; Qiu, Q.; Gill, S. C.; Jayasena, S. D. Nucleic Acid Res. 1994, 22, 5229-5234.
3. (c) McGee, D. P. C.; Vargeese, C.; Zhai, Y.; Kirschenheuter, G. P.; Settle, A.; Siedem, C. R.; Pieken, W. A. Nucleosides Nucleotides 1995, 1329-1339.
4. (a) Falck, J. R.; Yu, J.; Cho, H.-S. Tetrahedron Lett 1994, 35, 5997-6000.
5. (b) Cho, H.-S.; Yu, J.; Falck, J. R. J. Am. Chem Soc. 1994, 116, 8354-8355.
6. Pavlik, F. J. Perfluorotertiaryalkyl Ethers. U.S. Patent no. 3,981,928.
7. (a) For a comprehensive review of the Mitsunobu Reaction, see: Hughes, D. L. Org. React. 1992, 42, 335-656.
8. (b) For recent applications in carbon-carbon bond formation, see: Falck, J. R.; Yu, J. Tetrahedron Lett. 1992, 33, 6723-6726. Yu, J.; Cho, H.-S.; Falck, J. R. J. Org. Chem. 1993, 58, 5892-5894.
9. (b) For recent applications in carbon-carbon bond formation, see: Falck, J. R.; Yu, J. Tetrahedron Lett. 1992, 33, 6723-6726. Yu, J.; Cho, H.-S.; Falck, J. R. J. Org. Chem. 1993, 58, 5892-5894.
10. (c) For a recent application in the formation of aryl glycosides, see: Roush, W. R.; Lin, X. J. Org. Chem. 1991, 56, 5740-5742.
11. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper and Row: New York, 1987; Third Ed, p 300.
12. Henne, A. L.; Francis, W. C. J. Am. Chem. Soc. 1953, 75, 991-992.
13. a threshold above which acids are not deprotonated to a sufficient extent for efficient Mitsunobu reaction to occur at ambient temperatures.
14. For N-hydroxyphthalimide alkylation, see: Rougny, A.; Daudon, M. Bull. Soc. Chim. Fr. 1976, 833-838.