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10/2008: pages 213 - 233; , ISBN: 9783527623389
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Annalen der Chemie und Pharmacie 07/2006; 2006(18):4224 - 4230. · 3.10 Impact Factor
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ABSTRACT: A new chemoenzymatic method for the preparation of an intermediate of (-)-Paroxetine is reported. Cyclic anhydrides are used as acylating agents in the lipase-catalyzed esterification of trans-4-(4'-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine in organic solvents. The best enantioselectivities are obtained with two different lipases from Candida antarctica. These two lipases show opposite stereochemical preference in these processes, so that both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer is an intermediate for the synthesis of (-)-Paroxetine.
The Journal of Organic Chemistry 05/2003; 68(8):3333-6. · 4.45 Impact Factor
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ABSTRACT: Biocatalysis offers a clean and ecological way to perform chemical processes, in mild reaction conditions and with high degree of selectivity. The use of enzymes, specially lipases, in organic solvents proves an excellent methodology for the preparation of single-isomer chiral drugs. This review covers some general aspects and representative examples of the use of lipases for the enantioselective or regioselective preparation of alcohol and amine intermediates in the synthesis of pharmaceuticals.
Journal of Molecular Catalysis B: Enzymatic.
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Tetrahedron. 62(14):3284-3291.
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Tetrahedron Asymmetry 18(8):994-1002. · 2.65 Impact Factor
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Tetrahedron. 49(19):4007-4014.
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Tetrahedron Asymmetry 15(2):341-345. · 2.65 Impact Factor
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ABSTRACT: Optically active aliphatic ω-hydroxycyanohydrins are valued materials in organic synthesis. We describe herein the effect of the different reaction parameters as organic solvent, temperature, concentration of enzyme or concentration of buffer in the (R)-oxynitrilase-catalyzed synthesis of optically enriched aliphatic ω-hydroxycyanohydrins from 4-hydroxybutanal and 5-hydroxypentanal.
Journal of Molecular Catalysis B: Enzymatic.
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Tetrahedron Asymmetry 8(7):995-997. · 2.65 Impact Factor
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Tetrahedron Asymmetry 13(23):2577-2582. · 2.65 Impact Factor
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ABSTRACT: The preparation of (S)-2-cyanopiperidine 4 provides a new access to 2-substituted piperidines. This synthesis is based on an enantioselective (R)-oxynitrilase-catalyzed reaction for the preparation of (R)-(+)-6-bromo-2-hydroxyhexanenitrile 1 and the subsequent cyclization of this compound to yield the piperidine ring. The utilization of 4 as the starting material for the synthesis of (S)-2-aminomethylpiperidine 6, (R)-(−)-coniine 10 and (S)-(−)-pipecolic acid 13 is also described.
Tetrahedron: Asymmetry.
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ABSTRACT: Optically active ω-bromocyanohydrins are easily synthesized through an enantioselective (R)-oxynitrilase-catalyzed reaction from their corresponding ω-bromoaldehydes. These cyanohydrins are starting materials for the preparation of medium size nitrogen heterocycles. The reduction of (R)-(+)-5-bromo-2-hydroxypentanenitrile affords, in one-pot, piperidin-3-ol. Azepan-3-ol and azocan-3-ol are readily obtained from their corresponding cyanohydrins in high enantiomeric excesses.
Tetrahedron: Asymmetry.