Rapid synthesis of substituted 5-phenyl-1,3-dioxolan-4-ones under microwave-induced solvent-free conditions

Tetrahedron Letters

Volumn 44, Issue 12, 2003, Pages 2573-2576

  Ferrett, Rochelle R ^a   Hyde, Michael J ^a   Lahti, Kimberly A ^a   Friebe, Timothy L ^a  

^a EASTERN MICHIGAN UNIVERSITY   (United States)

Author keywords

Condensation; Dioxolane; Microwave induced; Solvent free conditions

Indexed keywords

ALDEHYDE; KETONE DERIVATIVE; MANDELIC ACID; SOLVENT;

ARTICLE; COLUMN CHROMATOGRAPHY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037450938     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00280-6     Document Type: Article

References (24)

1. Grover P.T., Bhongle N.N., Wald S.A., Senanayake C.H. J. Org. Chem. 65:2000;6283-6287.
2. Heckmann B., Mioshowski C., Lumin S., Falck J.R., Wei S., Capdevila J.H. Tetrahedron Lett. 37:1996;1425-1428.
3. Barbaro G., Battaglia A., Guerrini A., Bertucci C. Tetrahedron: Asymmetry. 8:1997;2527-2531.
4. Barbaro G., Battaglia A., Guerrini A. J. Org. Chem. 64:1999;4643-4651.
5. Mase T., Houpis I.N., Akao A., Dorziotis I., Emerson K., Hoang T., Iida T., Itoh T., Kamei K., Kato S., Kato Y., Kawasaki M., Lang F., Lee J., Lynch J., Maligres P., Molina A., Nemoto T., Okada S., Reamer R., Song J.Z., Tschaen D., Wada T., Zewge D., Volante R.P., Reider P.J., Tomimoto K. J. Org. Chem. 66:2001;6775-6786.
6. Petasis N.A., Lu S.-P. J. Am. Chem. Soc. 117:1995;6394-6395.
7. Mashraqui S.H., Kellogg R.M. J. Org. Chem. 49:1984;2513-2516.
8. Heckmann B., Mioskowski C., Bhatt R.K., Falck J.R. Tetrahedron Lett. 37:1996;1421-1424.
9. Heckmann B., Mioskowski C., Yu J., Falck J.R. Tetrahedron Lett. 33:1992;5201-5204.
10. Hoye T.R., Peterson B.H., Miller J.D. J. Org. Chem. 52:1987;1351-1353.
11. Pearson W.H., Cheng M.-C. J. Org. Chem. 52:1987;1353-1355.
12. Gorla F., Venanzi L.M. Helv. Chim. Acta. 73:1990;690-697.
13. Ott J., Tombo G.M.R., Schmid B., Venanzi L.M., Wang G., Ward T.R. Tetrahedron Lett. 30:1989;6151-6154.
14. Noyori R., Tsunoda T., Suzuki M. Tetrahedron Lett. 21:1980;1357.
15. Farines M., Soulier J. Bull. Soc. Chim. Fr. 1970;332-340.
16. Chapel N., Greiner A., Ortholand J.-Y. Tetrahedron Lett. 32:1991;1441-1442.
17. For recent reviews, see: (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223; (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283; (c) de la Hoz, A.; Diaz-Ortis, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659-3673; (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870; (e) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234; (f) Caddick, S. Tetrahedron 1995, 51, 10403-10432.
18. For recent reviews, see: (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223; (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283; (c) de la Hoz, A.; Diaz-Ortis, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659-3673; (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870; (e) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234; (f) Caddick, S. Tetrahedron 1995, 51, 10403-10432.
19. For recent reviews, see: (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223; (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283; (c) de la Hoz, A.; Diaz-Ortis, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659-3673; (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870; (e) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234; (f) Caddick, S. Tetrahedron 1995, 51, 10403-10432.
20. For recent reviews, see: (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223; (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283; (c) de la Hoz, A.; Diaz-Ortis, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659-3673; (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870; (e) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234; (f) Caddick, S. Tetrahedron 1995, 51, 10403-10432.
21. For recent reviews, see: (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223; (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283; (c) de la Hoz, A.; Diaz-Ortis, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659-3673; (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870; (e) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234; (f) Caddick, S. Tetrahedron 1995, 51, 10403-10432.
22. For recent reviews, see: (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223; (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283; (c) de la Hoz, A.; Diaz-Ortis, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659-3673; (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870; (e) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234; (f) Caddick, S. Tetrahedron 1995, 51, 10403-10432.
23. The major isomer (cis) has been well established. See for example Ref. 6 and Seebach D., Naef R., Calderari G. Tetrahedron. 40:1984;1313-1324.
24. All compounds gave spectroscopic data consistent with their structures.