Synthesis of new asymmetric phosphonylated thiazolines and their use in olefination reactions

Synthesis

Volumn , Issue 8, 2000, Pages 1143-1147

  Leflemme, Nicolas ^a   Marchand, Patrice ^a   Gulea, Mihaela ^a   Masson, Serge ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

Dithioester; Horner Wadsworth Emmons reaction; Mitsunobu reaction; Phosphonate; Thiazoline; Thioamide

Indexed keywords

OXAZOLINE DERIVATIVE; THIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0033927018     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6324     Document Type: Article

References (25)

1. Lutomski, K. A.; Meyers, A. I. Asymmetric Synthesis via Chiral Oxazolines. In Asymmetric Synthesis, Vol. 3; Academic Press: New York, 1984, p 213. Pfaltz, A. Synlett 1999, 835. Reuman, M.; Meyers, A. I. Tetrahedron Lett. 1985, 41, 837 Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
2. Lutomski, K. A.; Meyers, A. I. Asymmetric Synthesis via Chiral Oxazolines. In Asymmetric Synthesis, Vol. 3; Academic Press: New York, 1984, p 213. Pfaltz, A. Synlett 1999, 835. Reuman, M.; Meyers, A. I. Tetrahedron Lett. 1985, 41, 837 Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
3. Lutomski, K. A.; Meyers, A. I. Asymmetric Synthesis via Chiral Oxazolines. In Asymmetric Synthesis, Vol. 3; Academic Press: New York, 1984, p 213. Pfaltz, A. Synlett 1999, 835. Reuman, M.; Meyers, A. I. Tetrahedron Lett. 1985, 41, 837 Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
4. Lutomski, K. A.; Meyers, A. I. Asymmetric Synthesis via Chiral Oxazolines. In Asymmetric Synthesis, Vol. 3; Academic Press: New York, 1984, p 213. Pfaltz, A. Synlett 1999, 835. Reuman, M.; Meyers, A. I. Tetrahedron Lett. 1985, 41, 837 Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
5. Jalal, M. A. F.; Hossain, M. B.; van der Helm, D.; Sanders-Loehr, J.; Actis, L. A.; Crosa, J. H. J. Am. Chem. Soc. 1989, 111, 292.
6. Gerwick, W. H.; Proteau, J.; Nagle, D. G.; Hamel, E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994, 59, 1243. Muir, J. C; Pattenden, G.; Ye, T. Tetrahedron Lett. 1998, 39, 2861.
7. Gerwick, W. H.; Proteau, J.; Nagle, D. G.; Hamel, E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994, 59, 1243. Muir, J. C; Pattenden, G.; Ye, T. Tetrahedron Lett. 1998, 39, 2861.
8. Wipf, P.; Venkatraman, S. Synlett 1997, 1; and references cited therein.
9. Hayashi, K.; Sato, C.; Hiki, S.; Kumagai, T.; Tamai, S.; Abe, T.; Nagao, Y. Tetrahedron Lett. 1999, 40, 3761.
10. Caujolle, R.; Baziard-Mouysset; Favrot, J. D.; Payard, M.; Loiseau, P. R. Eur. J. Med. Chem. Chim. Ther. 1993, 28, 29.
11. Ehrler, J.; Farooq, S. Synlett 1994, 702.
12. Meyers, A. I.; Munavu, R.; Durandetta, S Tetrahedron Lett. 1972, 37, 3929.
13. Elliot, M. C.; Monk, A. E.; Kruiswijk, E.; Hibbs, D. E.; Jenkins, L.; Jones, D. V. Synlett 1999, 1379.
14. Meyers, A. I.; Shipman, M. J. Org. Chem. 1991, 56, 7098. Chesney, A.; Bryce, M. R. Tetrahedron: Asymmetry 1996, 7, 3247. Chesney, A.; Bryce, M. R. Batsanov, A. S.; Howard, J. A. K.; Goldenberg, L. M. Chem. Commun. 1998, 677.
15. Meyers, A. I.; Shipman, M. J. Org. Chem. 1991, 56, 7098. Chesney, A.; Bryce, M. R. Tetrahedron: Asymmetry 1996, 7, 3247. Chesney, A.; Bryce, M. R. Batsanov, A. S.; Howard, J. A. K.; Goldenberg, L. M. Chem. Commun. 1998, 677.
16. Meyers, A. I.; Shipman, M. J. Org. Chem. 1991, 56, 7098. Chesney, A.; Bryce, M. R. Tetrahedron: Asymmetry 1996, 7, 3247. Chesney, A.; Bryce, M. R. Batsanov, A. S.; Howard, J. A. K.; Goldenberg, L. M. Chem. Commun. 1998, 677.
17. The method is described with phosphonodithioformate and β-bromoethylamine hydrochloride: see ref. (15).
18. Le Roy-Gouvernnec, S.; Masson, S. Synthesis 1995, 1393.
19. Nagasawa, H.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1981, 54, 2223. Tamaru, Y.; Hioki, T.; Kawamura, S.; Satomi, H.; Yoshida, Z. J. Am. Chem. Soc. 1984, 106, 3876. Tanaka, T.; Hashimoto, T.; Iino, K.; Sugimura, Y.; Miyadera, T. J. J. Chem. Soc., Chem. Commun. 1982, 713. Takahata, H.; Ohkura, E.; Ikuro, K.; Yamazaky, T. Synth. Commun. 1990, 20, 285.
20. Nagasawa, H.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1981, 54, 2223. Tamaru, Y.; Hioki, T.; Kawamura, S.; Satomi, H.; Yoshida, Z. J. Am. Chem. Soc. 1984, 106, 3876. Tanaka, T.; Hashimoto, T.; Iino, K.; Sugimura, Y.; Miyadera, T. J. J. Chem. Soc., Chem. Commun. 1982, 713. Takahata, H.; Ohkura, E.; Ikuro, K.; Yamazaky, T. Synth. Commun. 1990, 20, 285.
21. Nagasawa, H.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1981, 54, 2223. Tamaru, Y.; Hioki, T.; Kawamura, S.; Satomi, H.; Yoshida, Z. J. Am. Chem. Soc. 1984, 106, 3876. Tanaka, T.; Hashimoto, T.; Iino, K.; Sugimura, Y.; Miyadera, T. J. J. Chem. Soc., Chem. Commun. 1982, 713. Takahata, H.; Ohkura, E.; Ikuro, K.; Yamazaky, T. Synth. Commun. 1990, 20, 285.
22. Nagasawa, H.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1981, 54, 2223. Tamaru, Y.; Hioki, T.; Kawamura, S.; Satomi, H.; Yoshida, Z. J. Am. Chem. Soc. 1984, 106, 3876. Tanaka, T.; Hashimoto, T.; Iino, K.; Sugimura, Y.; Miyadera, T. J. J. Chem. Soc., Chem. Commun. 1982, 713. Takahata, H.; Ohkura, E.; Ikuro, K.; Yamazaky, T. Synth. Commun. 1990, 20, 285.
23. Galéotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
24. Bulpin, A.; Le Roy-Gouvernnec, S.; Masson, S. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 89, 119.
25. Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326.