Electrochemical partial fluorination of organic compounds. 80. Synthesis of cyclic α-arylthio-α-monofluorophosphonate esters

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9614-9617

  Cao, Yi ^a   Hidaka, Asami ^a   Tajima, Toshiki ^a   Fuchigami, Toshio ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; SYNTHESIS (CHEMICAL);

ANODIC FLUORINATION; ELECTROAUXILIARY; RING-CLOSING OLEFIN METATHESIS (RCM);

ESTERS;

2 ALLYLOXY 3 FLUORO 3 PHENYLTHIO 4,7 DIHYDRO[1,2]OXAPHOSPHININE 2 OXIDE; ORGANIC COMPOUND; PHOSPHONIC ACID ESTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; ELECTROCHEMICAL ANALYSIS; FLUORINATION; ORGANIC CHEMISTRY; PRODUCT RECOVERY; RING CLOSING METATHESIS; SEQUENCE ANALYSIS; SYNTHESIS;

CYCLIZATION; ELECTROCHEMISTRY; ESTERS; FLUORINE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS;

EID: 27744527559     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051206r     Document Type: Article

References (38)

1. (a) Darrow, J. W.; Drueckhammer, D. G. J. Org. Chem. 1994, 59, 2976-2985.
2. (b) Hannessian, S.; Galeotti, N.; Rosen, P.; Olva, G.; Babu, S. Bioorg. Med. Chem. 1994, 23, 2763.
3. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1998, 57, 785.
4. (a) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942.
5. (b) Wang, Q.; Pfeiffer, B.; Tucker, G. C.; Royer, J.; Husson, H.-P. Bioorg. Med. Chem. Lett. 1997, 7, 2477
6. (c) Gao, J.; Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 9538.
7. (d) Natchev, I. A. Bull. Chem. Soc. Jpn. 1988, 61, 3705 and 3711.
8. (e) Natchev, I. A. J. Chem. Soc., Perkin Trans. 1 1989, 125.
9. See, for example: (a) Burke, T. R., Jr.; Kole, H. K.; Roller, P. P. Biochem. Biophys. Res. Commun. 1994, 204, 129-134.
10. (b) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 172-184.
11. (c) Higashimoto, Y.; Saito, S.; Tong, X.-H.; Hong, A.; Sakaguchi, K.; Appella, E.; Anderson, C. W. J. Biol. Chem. 2000, 275, 23199-23203.
12. (a) Lequeux, T.; Lebouc, F.; Lopin, C.; Yang, H.; Gouhier, G.; Piettre, S. R. Org. Lett. 2001, 3, 185-188.
13. (b) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Chen, M. J. Tetrahedron 1998, 54, 1691-1714.
14. See, for example: (a) Berkowitz, D. B.; Bose, M.; Pfannenstied, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498-4508.
15. (b) Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001, 112, 13-33.
16. Annedi, S. C.; Majumder, K.; Wei, L.; Oyiliagu, C. E.; Samson, S.; Kotra, L. P. Bioorg. Med. Chem. 2005, 13, 2943-2958.
17. (a) Smith, M. S.; Burke, T. R. Tetrahedron 1994, 35, 551-554.
18. (b) Solas, D.; Hale, R. D.; Patel, D. V. J. Org. Chem. 1996, 61, 1537-1539.
19. (a) Fuchigami, T. Organic Electrochemistry, 4th ed.; Lund, H., Hammerich, O., Eds.; Marcel Dekker: New York, 2000; Chapter 25.
20. (b) Suzuki, K.; Fuchigami, T. J. Org. Chem. 2004, 69, 1276-1282.
21. (c) Dawood, K. M.; Fuchigami, T. J. Org. Chem. 2004, 69, 5302-5306.
22. (d) Hasegawa, M.; Ishii, H.; Fuchigami, T. Green Chem. 2003, 5, 512-515.
23. For recent reviews on RCM, see: (a) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
24. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
25. (c) Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 10103-10109.
26. (d) Grubbs, R. H. Tetrahedron 2004, 60, 7117-7140.
27. (a) Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9858-9859.
28. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
29. (a) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060.
30. (b) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2001, 3, 3285-3288.
31. Spagnol, G.; Heck, M.-P.; Nalan, S. P.; Mioskowski, C. Org. Lett. 2002, 4, 1767-1770.
32. Butt, A. H.; Percy, J. M.; Spencer, N. S. Chem. Commun. 2000, 1691-1692.
33. Skropeta, D.; Schmidt, R. R. Tetrahedron: Asymmetry 2003, 14, 265-273.
34. Moore, J. D.; Sprott, K. T.; Hanson, P. R. Synlett 2001, 605-608.
35. Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; Marel, G. A.; Boom, J. H. Tetrahedron Lett. 2001 42, 8231-8233.
36. Lal, G. S. J. Org. Chem. 1993, 58, 2791-2796.
37. (a) Umemoto, T.; Tomizawa, G. Bull. Chem. Soc. Jpn. 1986, 59, 3625-3629.
38. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563-6570.