Optically active trans-2-aminocyclopentanols: Chemoenzymatic preparation and application as chiral ligands

Biotechnology Journal

Volumn 1, Issue 7-8, 2006, Pages 835-841

  González Sabín, Javier ^a   Gotor, Vicente ^a   Rebolledo, Francisca ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Amino alcohols; Lipase; Transesterification

Indexed keywords

AMINO ALCOHOLS; AS-LIGANDS; CHEMICAL YIELDS; CHIRAL LIGAND; DIETHYLZINC; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE ADDITION; HYDROXYL GROUPS; LIPASE-CATALYZED; OPTICALLY ACTIVE;

ALCOHOLS; ALDEHYDES; LIPASES; TRANSESTERIFICATION;

LIGANDS;

ACETIC ACID DERIVATIVE; IMMOBILIZED ENZYME; PENTANOL; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CHEMISTRY; ENZYMOLOGY; ESTERIFICATION; ISOMERISM; LIGHT; RADIATION EXPOSURE;

ACETATES; BURKHOLDERIA CEPACIA; CATALYSIS; ENZYMES, IMMOBILIZED; ESTERIFICATION; ISOMERISM; LIGHT; LIPASE; PENTANOLS;

EID: 39049175104     PISSN: 18606768     EISSN: 18607314     Source Type: Journal    
DOI: 10.1002/biot.200600035     Document Type: Article

References (22)

1. Ager, D. J., Prakash, I., Schaad, D. R., 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis. Chem. Rev. 1996, 96, 835-875.
2. Noyori, R., Kitamura, M., Enantioselective addition of organometallic reagents to carbonyl compounds: transfer, duplication and intensification of chirality. Angew. Chem. Int. Ed. Engl. 1991, 30, 34-48.
3. Tomioka, K., Asymmetric synthesis utilizing external chiral ligands. Synthesis 1990, 541-549.
4. Witiak, D. T., Inbasekaran, M. N., Pharmaceuticals, optically active. Kirk-Othmer Encycl. Chem. Technol. 1982, 17, 311-345.
5. Jacques, J., Collet, A., Wilen, S. H., Enantiomers, Racemates and Resolutions, John Wiley & Sons, New York 1981.
6. Faber, K., Biotransformations in Organic Chemistry, 5th edn., Springer-Verlag, Heidelberg 2004.
7. Bornscheuer, U. T., Kazlauskas, R. J., Hydrolases in Organic Synthesis - Regio- and stereoselective Biotransformations, 2nd edn., Wiley-VCH, Weinheim 2005.
8. Luna, A., Astorga, C., Fülop, F., Gotor, V., Enzymatic resolution of (±)-cis-2-aminocyclopentanol and (±)-cis-2-aminocyclohexanol. Tetrahedron Asymmetry 1998, 9, 4483-4487.
9. Sekar, G., Kamble, R. M., Singh, V. K., Enantiomerically pure N-aryl-®-amino alcohols by enzymatic resolution. Tetrahedron Asymmetry 1999, 10, 3663-3666.
10. Luna, A., Maestro, A., Astorga, C., Gotor, V., Enzymatic resolution of (±)-cis- and (±)-trans-1-aminoindan-2-ol and (±)-cis- and (±)-trans-2-aminoindan-1-ol. Tetrahedron Asymmetry 1999, 10, 1969-1977.
11. Clariana, J., García-Granda, S., Gotor, V., Gutiérrez-Fernández, A. et al., Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated ®-ketoester alkylation and enzyme-based aminoalcohol resolution. Tetrahedron Asymmetry 2000, 11, 4549-4557.
12. González-Sabín, J., Gotor, V., Rebolledo, F., Chemoenzymatic preparation of optically active ®-amino cyclohexanols and their application in the enantioselective addition of diethylzinc to benzaldehyde. Tetrahedron Asymmetry 2004, 15, 1335-1341.
13. Marshall, I. G., Parsons, S. M., The vesicular acetylcholine transport system. Trends Neurosci. 1987, 10, 174-177.
14. Rogers, G. A., Parsons, S. M., Anderson, D. C., Nilsson, L. M. et al., Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol). J. Med. Chem. 1989, 32, 1217-1230.
15. Quirós, M., Rebolledo, F., Gotor, V., Bioreduction of 2-oxocyclopentanecarboxamides: syntheses of optically active 2-aminomethyland 2-aminocyclopentanols. Tetrahedron Asymmetry, 1999, 10, 473-486.
16. Chakraborti, A. K., Rudrawar, S., Kondaskar, A., Lithium bromide, an inexpensive and efficient catalyst for opening of epoxide rings by amines at room temperature under solvent-free condition. Eur. J. Org. Chem. 2004, 3597-3600.
17. Najmodin, A., Mohammad R. S., Solid lithium perchlorate as a powerful catalyst for the synthesis of ®-amino alcohols under solventfree conditions. Can. J. Chem. 2005, 83, 505-507.
18. Chen, C. S., Fujimoto, Y., Girdaukas, G., Sih, C. J., Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 1982, 104, 7294-7299.
19. Lemaire-Audoire, S., Savignac, M., Genêt, J. P., Bernard, J. -M., Selective deprotection of allyl amines using palladium. Tetrahedron Lett. 1995, 36, 1267-1270.
20. Kazlauskas, R. J., Weissfloch, A. N. E., Rappaport, A. T., Cuccia, L. A., A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase de Pseudomonas cepacia, and lipase from Candida rugosa. J. Org. Chem. 1991, 56, 2656-2665.
21. Dale, J. A., Dull, D. L., Mosher, H. S., 〈 -Methoxy-〈 -trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J. Org. Chem. 1969, 34, 2543-2549.
22. Sosa-Rivadeneyra, M., Muñoz-Muñiz, O., Anaya de Parrodi, C., Quintero, L., Juaristi, E., Molecular modeling of salt (lithium chloride) effects on the enantioselectivity of diethylzinc addition to benzaldehyde in the presence of chiral ®-amino alcohols. J. Org. Chem. 2003, 68, 2369-2375.