Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol

Tetrahedron Asymmetry

Volumn 14, Issue 21, 2003, Pages 3313-3319

  Serra, Stefano ^a   Brenna, Elisabetta ^a   Fuganti, Claudio ^a   Maggioni, Francesco ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ISOPIPERITOL; ISOPULEGOL; MENTHOL; PIPERITOL; TERPENE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ISOMER; KINETICS; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0142196048     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.010     Document Type: Article

References (29)

1. Pybus D.H., Sell C.S. The Chemistry of Fragrances. 1999;67-76 The Royal Society of Chemistry, Cambridge.
2. Noboru, S.; Takaji, M. European Patent EP 1153908A2, 14/11/2001.
3. Bain, J. P.; Hunt, H. G.; Klein, E. A.; Booth, A. B. United States Patent US 2972632, 21/02/1961.
4. Brenna E., Fuganti C., Serra S. Tetrahedron: Asymmetry. 14:2003;1-42.
5. Yamamoto, T. European Patent EP 0694514A2, 31/01/1996.
6. Akutagawa S. Collins A.N., Sheldracke G.N., Crosby J. Chirality in Industry. 1992;313-323 John Wiley.
7. Vorlova S., Bornscheuer U.T., Gatfield I., Hilmer J.-M., Bertram H.-J., Schmid R.D. Adv. Synth. Catal. 344:2002;1152-1155.
8. Gatfield, I.; Hilmer, J.-M.; Bornscheuer, U. T.; Schmid, R. D.; Vorlova, S. European Patent EP1223223A1, 17/07/2002.
9. Chaplin, J. A.; Gardiner, N. S.; Mitra, R. K.; Parkinson, C. J.; Portwig, M.; Mboniswa, B. A.; Dickson, M. D. E.; Brady, D.; Marais, S. F.; Reddy, S. International Patent WO02/36795A2, 10/05/2002.
10. Lin G., Lin W.-Y. Tetrahedron Lett. 39:1998;4333-4336.
11. Wu W.-H., Akoh C.C., Phillips R.S. Enzyme Microb. Technol. 18:1996;536-539.
12. Persichetti R.A., Lalonde J.J., Govardhan C.P., Khalaf N.K., Margolin A.L. Tetrahedron Lett. 37:1996;6507-6510.
13. Langrand G., Baratti J., Buono G., Triantaphylides C. Tetrahedron Lett. 27:1986;29-32.
14. Langrand G., Secchi M., Buono G., Baratti J., Triantaphylides C. Tetrahedron Lett. 26:1985;1857-1860.
15. Serra S., Fuganti C. Helv. Chim. Acta. 85:2002;2489-2502.
16. Friedrich D., Bohlmann F. Tetrahedron. 44:1988;1369-1392.
17. Corey E.J., Ensley H.E., Suggs J.W. J. Org. Chem. 41:1976;380-381.
18. Eschinasi E.H. J. Org. Chem. 35:1970;2010-2012.
19. Schenck G.O., Gollnick K., Buchwald G., Schroeter S., Ohloff G. Liebigs Ann. Chem. 674:1964;93-117.
20. Macbeth A.K., Shannon J.S. J. Chem. Soc. 1952;2852-2856.
21. Guillon J., Rioult J.-P., Robba M. Flavour Fragr. J. 15:2000;223-224. and references cited therein.
22. Marshall J.A., Lebreton J. J. Org. Chem. 53:1988;4108-4112.
23. Fisher, R. Deutsches Patent 2305629, 14/08/1974.
24. Anglea T.A., Pinder A.R. Tetrahedron. 43:1987;5537-5543.
25. Banks R.E., Miller J.A., Nunn M.J., Stanley P., Weakley T.J.R., Ullah Z. J. Chem. Soc., Perkin Trans. 1. 1981;1096-1102.
26. Kocienski P.J., Pontiroli A., Qun L. J. Chem. Soc., Perkin Trans. 1. 2001;2356-2366.
27. Juo R.-R., Herz W. J. Org. Chem. 50:1985;700-703.
28. Catin A., Lull C., Primo J., Miranda M.A., Primo-Yufera E. Tetrahedron: Asymmetry. 12:2001;677-683.
29. Hiroi K., Umemura M. Tetrahedron. 49:1993;1831-1840.