A novel route to 3-(O,O-diethylphosphoryl)-2,3-dihydrofurans via rhodium-catalyzed heterocycloaddition reaction

Synthetic Communications

Volumn 34, Issue 18, 2004, Pages 3251-3258

  Gong, Denghuang ^a   Zhang, Ling ^a   Yuan, Chengye ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Heterocycloaddition; Phosphoryl dihydrofurane; Rhodium catalyzed

Indexed keywords

3 (O,O DIETHYLPHOSPHORYL) 5 ETHOXY 2 METHYL 2,3 DIHYDROFURAN; 5 BUTOXY 3 (O,O DIETHYLPHOSPHORYL) 2 METHYL 2,3 DIHYDROFURAN; 5 BUTOXY 3 (O,O DIETHYLPHOSPHORYL) 2 PHENYL 2,3 DIHYDROFURAN; 5 BUTOXY 3 (O,O DIETHYLPHOSPHORYL) 2 TRIFLUOROMETHYL 2,3 DIHYDROFURAN; 5 ISOBUTOXY 3 (O,O DIETHYLPHOSPHORYL) 2 METHYL 2,3 DIHYDROFURAN; 5 ISOBUTOXY 3 (O,O DIETHYLPHOSPHORYL) 2 PHENYL 2,3 DIHYDROFURAN; 5 ISOBUTOXY 3 (O,O DIETHYLPHOSPHORYL) 2 TRIFLUOROMETHYL 2,3 DIHYDROFURAN; FURAN DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 5444236608     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200030537     Document Type: Article

References (37)

1. (a) Engel, R. Chem. Rev. 1977, 77, 349;
2. (b) Castagnino, E.; Corsano, S.; Serena, B. Gazz. Chim. Ital. 1983, 113, 97;
3. (c) Hanessian, S.; Bennani, Y.L.; Delorme, D. Tetrahedron Lett. 1990, 31, 6461.
4. (a) Filler, R.; Kobayashi, Y. Biomedical Aspects of Fluorine Chemistry; Kodansha: Tokyo, 1982;
5. (b) Huklicky, M. Chemistry of Organo Fluorine Compounds; Ellis Horwood: New York, 1976;
6. (c) Chambers, R.D.; Sarget, C.R. Adv. Heterocycle Chem. 1981, 1, 28.
7. (a) Filler, R.; Kobayashi, Y. Biochemical Aspects of Fluorine Chemistry; Kodasha Ltd.: Tokyo and Elsevier Biomedical: Amsterdam, New York, Oxford, 1982;
8. (b) Welch, J.T. Tetrahedron 1987, 43, 3123.
9. (a) Engel, R. Handbook of Organophosphorus Chemistry; Marcel Dekker: New York, 1992;
10. (b) Kafaski, P.; Lejczak, B. Phosphorus Sulfur 1991, 63, 193-215;
11. (c) Toy, A.D.F.; Walsh, E.N. Phosphorus Chemistry in Everyday Living; American Chemical Society: Washington, DC, 1987, 333.
12. (a) Donnyelly, D.M.X.; Benasse, R. In Comprehensive Heterocyclic Chemistry; Katrizky, A.R., Rees, C.W., Scriven, E.F.V., Eds.; Pergamon: New York, 1996;
13. (b) Nakaishi, K. Natural Products Chemistry; Kodansha, Ltd.: Toyko, 1974.
14. (a) Arma, D.K.; Kundu, A.; Baati, R.; Mioskowski, C.; Falck, J.R. Org. Lett. 2001, 4, 1387-1389;
15. (b) Hou, X.; Yang, Z.; Wong, H. In Progress in Heterocyclic Chemistry; Gribble, G.W., Gilchrist, T.L., Eds.; Pergamon: UK, 2002; Vol. 14, 139-179;
16. (c) Lipshuts, B.H. Chem. Rev. 1986, 86, 795;
17. (d) Marshall, J.A. Recent Res. Dev. Org. Chem. 1997, 1, 1;
18. (e) Marshall, J.A.; Devender, E.A.J. Org. Chem. 2001, 66, 8037;
19. (f) Wu, W.; Wang, M.; Zhu, J.; Zhou, W.; Hu, Z.; Ji, Z.J. Nat. Prod. 2001, 64, 364.
20. (a) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Synthesis 1981, 56;
21. (b) Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909;
22. (c) Osuka, A.; Ohmasa, N.; Yoshida, Y.; Suzuki, H. Synthesis 1983, 69;
23. (d) Lu, X.; Zhu, J. Synthesis 1987, 726.
24. (a) Redmore, D. Chem Rev. 1971, 71, 315-337;
25. (b) Pevzner, L.M.; Ignat'ev, V.M.; Ionin, B.I. Zhur. Obshch. Khim. 1994, 64, 1108;
26. (c) Lee, C.; Oh, D.Y. Heterocycles 1996, 43, 1171-1174;
27. (d) Bestmann, H.J.; Lehnen, H. Tetrahedron Lett. 1991, 32 (34), 4279-4282;
28. (e) Yu, D.; Tirakyan, M.R.; Panosyan, G.A.; Denisenko, V.I.; Badanyan, S.O. Zh. Obshch. Khim. 1998, 58 (6), 1240-1247;
29. (f) Malenko, D.M.; Simurova, N.V.; Randina, L.V.; Sinitsa, A.D. Zh. Obshch. Khim. 1989, 59 (8), 1906-1907;
30. (g) Truel, I.; Mohamed-Hachi, A.; About-Jaudet, E.; Collignon, N. Synth. Commun. 1997, 22 (7), 1165-1171.
31. Doyle, M.P.; McKewey, M.A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wily: New York, 1998; 206-209.
32. Gong, D.; Zhang, L.; Yuan, C. Synth. Commun. 2004, 34 (18), 3259-3264.
33. (a) Regiz, M.; Anschütz, W.; Liedhegener, A. Chem. Ber. 1968, 101 (11), 3734-3743;
34. (b) Lee, J.C.; Yuk, J.Y. Synth. Commun. 1995, 25 (10), 1511-1515;
35. (c) Alloum, A.B.; Villemin, D. Synth. Commun. 1989, 19 (13,14), 2567-2571.
36. (a) Searle, N.E. Org. Synth. 1956, 36, 25;
37. (b) Gajda, T.; Matusiak, M. Synth. Commun. 1992, 22 (15), 2193-2203.