Lipase-catalyzed selective benzoylation of 1,2-diols with vinyl benzoate in organic solvents

Tetrahedron Asymmetry

Volumn 14, Issue 20, 2003, Pages 3197-3201

  Ciuffreda, Pierangela ^a   Alessandrini, Laura ^a   Terraneo, Giancarlo ^a   Santaniello, Enzo ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; ORGANIC SOLVENT; PROPYLENE GLYCOL; TRIACYLGLYCEROL LIPASE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0842297075     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.07.003     Document Type: Article

References (30)

1. Drauz K., Waldmann H. Enzymes Catalysis in Organic Synthesis. 1995;VCH, Weinheim.
2. Andersch, P.; Berger, M.; Hermann, J.; Laumen, K.; Lobell, M.; Seemayer, R.; Waldinger, C.; Schneider, M. P. In Ester Synthesis via Acyl Transfer (Transesterification); Rubin, B.; Dennis, E. A., Eds. Methods in Enzymology. Academic Press: New York, 1997; Vol. 286, pp. 406-443.
3. Carrea G., Riva S. Angew. Chem., Int. Ed. 39:2000;2226-2254.
4. Enzymes in non-Aqueous Solvents. Methods and Protocols; Vulfson, E. V.; Halling, P. J.; Holland, H. L., Eds.; Humana Press: Totowa, NJ, 2001.
5. Degueil-Castaing M., De Jeso B., Drouillard S., Maillard B. Tetrahedron Lett. 28:1987;953-954.
6. Wang Y.-F., Lalonde J.J., Momongan M., Bergbreiter D.E., Wong C.-H. J. Am. Chem. Soc. 110:1988;7200-7205.
7. Faber K., Riva S. Synthesis. 1992;895-910.
8. Theil F. Chem. Rev. 95:1995;2203-2227.
9. Stereoselective Biocatalysis; Patel, R. N., Ed. Marcel Dekker: New York, 2000.
10. Ema T., Maeno S., Takaya Y., Sakai T., Utaka M. J. Org. Chem. 61:1996;8610-8616. and references cited therein.
11. Vänttinen E., Kanerva L.T. Tetrahedron: Asymmetry. 8:1997;923-933.
12. Kawasaki M., Goto M., Kawabata S., Kodama T., Kometani T. Tetrahedron Lett. 40:1999;5223-5226.
13. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 1999;100 Wiley, New York.
14. Caddick S., McCarroll A.J., Sandham D.A. Tetrahedron. 57:2001;6305-6310. and references cited therein.
15. Yamazaki Y., Hosono K. Tetrahedron Lett. 31:1990;3895-3896.
16. Panza L., Brasca S., Riva S., Russo G. Tetrahedron: Asymmetry. 4:1993;931-932.
17. Tokuyama S., Yamano T., Aoki I., Takanohashi K., Nakahama K. Chem. Lett. 1993;741-744.
18. See for instance: Roche Molecular Biochemicals, Catalogue 2000-2001; p. 9.
19. Ciuffreda P., Casati S., Santaniello E. Tetrahedron Lett. 44:2003;3663-3665.
20. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543-2549.
21. Chen C.-S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294-7299.
22. Ohtani I., Kusumi T., Kasman Y., Kakisawa H. J. Am. Chem. Soc. 113:1991;4092-4096.
23. Shieh N., Price C.C. J. Org. Chem. 24:1959;1169.
24. Theil F., Ballschuh S., Kunath A., Schick H. Tetrahedron: Asymmetry. 2:1991;1031-1034.
25. Theil F., Weidner J., Ballschuh S., Kunath A., Schick H. Tetrahedron Lett. 34:1993;305-306.
26. Carrea G., Ottolina G., Riva S. Trends Biotechnol. 13:1995;63-70.
27. Still W.C., Kahn M., Mitra A. J. Org. Chem. 43:1978;2923-2925.
28. Sakai T., Wada K., Muratami T., Kohra K.,. Imajo N., Ooga Y., Tsuboi S., Takeda A., Utaka M. Bull. Chem. Soc. Jpn. 65:1992;631-638.
29. Reginato G., Ricci A., Roelens S., Scapecchi S. J. Org. Chem. 55:1990;5132-5139.
30. Ziegler T., Bien F., Jurisch C. Tetrahedron: Asymmetry. 9:1998;765-780.