Base-catalyzed ethanolysis of α-diethoxyphosphoryl-γ-lactones: A facile synthesis of cyclopropanecarboxylates

Synlett

Volumn , Issue 17, 2005, Pages 2648-2652

  Krawczyk, Henryk ^a   Wa̧sek, Katarzyna ^a   Kȩdzia, Jacek ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

lactones; Alkylation; Cyclopropanecarboxylates; Stereoselective synthesis; Wittig type cyclopropanation

Indexed keywords

3 BENZYL 3 DIETHOXYPHOSPHORYL 5 METHYLTETRAHYDROFURAN 2 ONE; 3 DIETHOXYPHOSPHORYL 5,5 DIMETHYL 4 (2 METHYLPROP 1 ENYL)TETRAHYDROFURAN 2 ONE; ALCOHOL; ALPHA DIETHOXYPHOSPHORYL GAMMA LACTONE; BETA (2 METHYL 1 PROPENYL) GAMMA,GAMMA DIMETHYL ALPHA DIETHOXYPHOSPHORYL GAMMA LACTONE; BETA BUTYL GAMMA,GAMMA DIMETHYL ALPHA DIETHOXYPHOSPHORYL GAMMA LACTONE; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; FURANONE DERIVATIVE; KETONE DERIVATIVE; LACTONE DERIVATIVE; N BUTYLMAGNESIUM BROMIDE; SODIUM; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 27444442451     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917116     Document Type: Article

References (27)

1. (a) Denney, D. B.; Boskin, M. J. J. Am. Chem. Soc. 1959, 81, 6330.
2. (b) Wadsworth, W. S.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733.
3. (c) Denney, D. B.; Vill, J. J.; Boskin, M. J. J. Am. Chem. Soc. 1962, 84, 3944.
4. (d) Tömösközi, I. Tetrahedron 1963, 19, 1969.
5. (e) Izydore, R. A.; Ghirardelli, R. G. J. Org. Chem. 1973, 38, 1790.
6. (f) Baboulene, M.; Sturtz, G. Phosphorus 1973, 2, 195.
7. (g) Fitzsimmons, B. J.; Fraser-Reid, B. Tetrahedron 1984, 40, 1279.
8. (h) Petter, R. C. Tetrahedron Lett. 1989, 30, 399.
9. (i) Petter, R. C.; Banerjee, S.; Englard, S. J. Org. Chem. 1990, 55, 3088.
10. (a) Wallace, P.; Warren, S. Tetrahedron Lett. 1985, 26, 5713.
11. (b) Wallace, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1988, 2971.
12. (c) Ayrey, P.; Warren, S. Tetrahedron Lett. 1989, 34, 4581.
13. (d) Nelson, A.; Warren, S. J. Chem. Soc., Perkin Trans, 1 1999, 3425.
14. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955.
15. (a) Reeve, C. D.; Crout, D. H. G.; Cooper, K.; Fray, M. J. Tetrahedron: Asymmetry 1992, 785.
16. (b) Ohta, A.; Sawamoto, D.; Jayasundera, K. P.; Kinoshita, H.; Inomata, K. Chem. Lett. 2000, 492.
17. Daremon, C.; Rambaud, R. Bull Soc. Chim. Fr. 1971, 294.
18. Giaocchino, F.; Bernd, S.; Wilfried, P. Z. Naturforsch., B: Chem. Sci. 1983, 38, 493.
19. 5P: C, 58.89; H, 7.10. Found: C, 59.02; H, 7.05.
20. (a) Janecki, T.; Kuś, A.; Krawczyk, H.; Blaszczyk, E. Synlett 2000, 611.
21. (b) Janecki, T.; Błaszczyk, E. Synthesis 2001, 403.
22. 5P: C, 55.25; H, 8.28. Found: C, 55.12; H, 8.20.
23. 2: C, 77.03; H, 8.31. Found: C, 76.89; H, 8.28.
24. Choi, S.-Y.; Newcomb, M. Tetrahedron 1995, 51, 657.
25. Rao, A. V. R.; Rao, M. N.; Garyali, K. Synth. Commun. 1984, 14, 557.
26. (a) Gerber, J. P.; Modro, T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroat. Chem. 1991, 2, 643.
27. (b) Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572.