An efficient and user-friendly strategy for the synthesis of cyclopropane and dihydrofuran rings from difunctional compounds

Synthesis

Volumn , Issue 10, 2006, Pages 1657-1663

  Mekonnen, Alemayehu ^a   Carlson, Rolf ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

Author keywords

dicarbonyl compounds; Conjugate addition initiated ring closure reaction; Cyclopropanation; Dihydrofurans; Ionic liquids

Indexed keywords

SOLVENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

Β-DICARBONYL COMPOUNDS; CONJUGATE-ADDITION-INITIATED RING-CLOSURE REACTION; CYCLOPROPANATION; DIHYDROFURANS; IONIC LIQUIDS;

PARAFFINS;

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 2 BROMO 2 CYCLOPENTENONE; CARBENE; CARBON; CYCLOPENTENONE DERIVATIVE; CYCLOPROPANE; DIHYDROFURAN DERIVATIVE; FURAN DERIVATIVE; IONIC LIQUID; PHOSPHATE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLVATION; SYNTHESIS; THERMOSTABILITY; VAPOR PRESSURE;

EID: 33744459775     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926459     Document Type: Article

References (26)

1. (a) Xu, L.; Li, L.; Xia, C.; Zhou, S.; Li, J. Tetrahedron Lett. 2004, 45, 1219.
2. (b) Sheldon, R. J. Chem. Soc., Chem. Commun. 2001, 2399.
3. (c) Handy, S. T.; Okello, M.; Dickenson, G. Org. Lett. 2003, 5, 2513.
4. (a) Yadav, J. S.; Reddy, B. V. S.; Baishya, G. J. Org. Chem. 2003, 68, 7098.
5. (b) Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Chem. Lett. 2003, 32, 988.
6. (a) Lebel, H.; Marcoux, J.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
7. (b) Lee, J.; Li, J.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301.
8. (c) Kumar, V. T.; Rao, S. K.; Narayana, L. V.; Dubey, P. K.; Aparna, V. Heterocycl. Commun. 2003, 9, 51.
9. (d) Alexakis, A.; March, S. J. Org. Chem. 2002, 67, 8753.
10. (a) Chen, C.; Xi, C.; Jiang, Y.; Hong, X. Tetrahedron Lett. 2004, 45, 6067.
11. (b) Wang, Y.; Zhao, X.; Li, Y.; Lu, L. Tetrahedron Lett. 2004, 45, 7775.
12. (c) Little, R. D.; Dawson, J. R. Tetrahedron Lett. 1980, 21, 2609.
13. (d) Prempree, P.; Radviroongit, S.; Thebtaranonth, Y. J. Org. Chem. 1983, 48, 3553.
14. (a) Chen, C.; Liao, Y.; Huang, Y. Tetrahedron 1989, 45, 3011.
15. (b) Li, A.; Dai, L.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
16. (a) Hagiwara, H.; Sato, K.; Nishino, D.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans, 1 2001, 2946.
17. (b) Hagiwara, H.; Sato, K.; Hoshi, T.; Ando, M. Tetrahedron Lett. 1997, 38, 2103.
18. Farina, F.; Maestro, M. C.; Martin, M. V.; Soria, M. L. Tetrahedron 1987, 43, 4007.
19. (a) Arai, S.; Nakayama, K.; Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 63, 9572.
20. (b) Arai, S.; Nakayama, K.; Suzuki, Y.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1998, 39, 9739.
21. (c) Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
22. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
23. (b) Wasserscheid, P.; Keim, W. Angew Chem. Int. Ed. 2000, 39, 3772.
24. Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410.
25. Lee, Y. R.; Kim, B. S.; Kim, D. H. Tetrahedron 2000, 56, 8845.
26. Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088.