A new and convenient route to optically active 2-phosphoryl-3-oxo-5-alkyl/- aryltetrahydrofurans and their reactions

European Journal of Organic Chemistry

Volumn , Issue 10, 2004, Pages 2253-2262

  Xu, Chengfu ^a   Zhang, Yonghui ^a   Yuan, Chengye ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Horner Wadsworth Emmons reactions; O H Insertion reaction; Rhodium catalyst; Tetrahydrofurans

Indexed keywords

2 DIETHOXYPHOSPHORYL 3 OXO 5 PHENYLTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 3 OXO 5 VINYLTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 5 (2 FURYL) 3 OXOTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 5 (4 ETHYLPHENYL) 3 OXOTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 5 (4 FLUOROPHENYL) 3 OXOTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 5 (4 METHOXYPHENYL) 3 OXOTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 5 (4 METHYLPHENYL) 3 OXOTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 5 ETHYL 3 OXOTETRAHYDROFURAN; 2 DIETHOXYPHOSPHORYL 5 METHYL 3 OXOTETRAHYDROFURAN; 5 (2 BROMOPHENYL) 2 DIETHOXYPHOSPHORYL 3 OXOTETRAHYDROFURAN; 5 (2,4 DICHLOROPHENYL) 2 DIETHOXYPHOSPHORYL 3 OXOTETRAHYDROFURAN; FURAN DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 4544384599     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400018     Document Type: Article

References (33)

1. [1a] L. D. Buyck, N. Menke, J. Louagie, Bull. Soc. Chim. Belg. 1991, 100, 187-189.
2. [1b] R. D. Guthrie, I. D. Jenkins, J. J. Watters, M. W. Wright, R. Yamasaki, Aust. J. Chem. 1982, 35, 2169-2173.
3. [1c] T. Sakakibara, T. Takamoto, T. Matsuzaki, H. Omi, U. W. Maung, R. Sudoh, Carbohydr. Res. 1981, 95, 291-298.
4. U. Hacksell, G. D. Daves, The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides, In Process in Medicinal Chemistry; Elsevier Science Publishers: London, 1985, vol. 22, 1-65.
5. [3a] A. M. Calter. C. Zhu, J. Org Chem 1999 64, 1415-1419.
6. [3b] A. M. Caller, C. Zhu, Tetrahedron Lett. 1997, 38, 3837-3840.
7. [3c] P. Albert, S. Marcus, Tetrahedron Lett. 1997, 38, 5087-5090.
8. [4a] R. P. Newton, D. Chiatante, D. Ghosh, G. A. Brenton, T. J. Wallon, Phytochemistry 1989, 28, 2243-2254.
9. [4b] W. G. Bentrude, J. Tomasz, Synthesis 1984, 1, 27-29.
10. [4c] A. Wolff, M. E. Burger, J. Am. Pharm. Assoc. 1959, 48, 56-59.
11. [4d] K. Yoshino, T. Kohno, T. Morita, G. Tsukamolo, J. Med. Chem. 1989, 32, 1528-1532.
12. [5a] F. Nicotra, L. Panza, G. Russo, A. Senaldi, N. Burlini, P. Tortora, J. Chem. Soc., Chem. Commun. 1990, 20, 1396-1397.
13. [5b] W. Putsch, F. Jerman, Liebigs Ann. Chem. 1985, 307-311.
14. [5c] R. D. Allan, J. R. Hanrahan, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, A. D. Mitrovic, J. Med. Chem. 1990, 33, 2905-2915.
15. [5d] K. Sasaki, Bull. Chem. Soc. Jpn. 1966, 39, 2703.
16. [6a] Y. H. Zhang, C. F. Xu, J. F. Li, C. Y. Yuan, Tetrahedron: Asymmetry 2003, 14, 63-70.
17. [6b] Y. H. Zhang, C. Y. Yuan, Z. Y. Li, Tetrahedron 2002, 58, 2973-2978.
18. [6c] Y. H. Zhang, Z. Y. Li, C. Y. Yuan, Tetradedron Lett. 2002, 43, 3247-3249.
19. E. Wada, S. Kanemasa, O. Tsuge, Bull. Chem. Soc. Jpn. 1989, 62, 860-868.
20. [8a] N. Farrell, J. Inorg. Biochem. 1981, 14, 261-265.
21. [8b] N. Petiniot, A. J. Anciaux, A. F. Noels, A. J. Hubert, P. Teyssie, Tetrahedron Lett. 1978, 14, 1239-1242.
22. [8c] R. Pellicciari, R. Fringuelli, P. Ceccherelli, E. Sisani, J. Chem. Soc., Chem. Commun. 1979, 21, 959-960.
23. [8d] I. N. Domnin, E. F. Zhuravleva, N. V. Pronina, Zh. Org. Khim. 1978, 14, 2323-2327.
24. [9a] K. Lee, D. F. Wiemer, J. Org. Chem. 1993, 58, 7808-7812.
25. [9b] K. Konno, K. Hashimoto, Y. Ohfune, H. Shirahama, T. Matsumoto, Tetrahedron Lett. 1986, 27, 607-610.
26. [9c] K. Konno, K. Hashimoto, Y. Ohfune, H. Shirahama, T. Matsumoto, J. Am. Chem. Soc. 1988, 110, 4807-4815.
27. [9d] T. Durand, O. Henry, A. Guy, A. Roland, J. P. Vidal, J. C. Rossi, Tetrahedron 2003, 59, 2485-2496.
28. [9e] H. Kiyota, D. J. Dixon, C. K. Luscombe, S. Hettstedt, S. V. Ley, Org. Lett. 2002, 4, 3223-3226.
29. [9f] Q. Zhang, A. Rivkin, D. P. Curran, J. Am. Chem. Soc. 2002, 124, 5774-5781.
30. [9g] D. L. Boger, S. Ichikawa, W. Zhong, J. Am. Chem. Soc. 2001, 123, 4161-4167.
31. [10a] M. J. Davies, C. J. Moody, R. J. Taylor, J. Chem. Soc., Perkin Trans. 1 1991, 1, 1-7.
32. [10b] C. J. Moody, E. H. B. Sie, J. J. Kulagowski, J. Chem. Soc., Perkin Trans. 1 1994, 5, 501-506.
33. L. W. McElwee, D. A. Dougherty, J. Am. Chem. Soc. 1984, 106, 3466-3474.