Molecules 2012, 17(8), 8955-8967; doi:10.3390/molecules17088955
Article

Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica

1 Institute of Chemistry of São Carlos, University of São Paulo, Av. Trabalhador São-carlense, 400, 13560-970, São Carlos, SP, Brazil 2 Department of Chemistry, Federal University of Goias, Campus Advanced of Catalão, Av. Dr. Lamartine Pinto de Avelar, 1120, 75704-020, Catalão, GO, Brazil
* Author to whom correspondence should be addressed.
Received: 24 April 2012; in revised form: 27 June 2012 / Accepted: 3 July 2012 / Published: 26 July 2012
(This article belongs to the Special Issue Biocatalysis and Biotransformations in Organic Synthesis)
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Abstract: The lipase B from Candida antarctica (Novozym 435®, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.
Keywords: kinetic resolution; lipase; Candida antarctica; aliphatic secondary alcohols

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MDPI and ACS Style

Ferreira, H.V.; Rocha, L.C.; Severino, R.P.; Porto, A.L.M. Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica. Molecules 2012, 17, 8955-8967.

AMA Style

Ferreira HV, Rocha LC, Severino RP, Porto ALM. Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica. Molecules. 2012; 17(8):8955-8967.

Chicago/Turabian Style

Ferreira, Hercules V.; Rocha, Lenilson C.; Severino, Richele P.; Porto, André L. M. 2012. "Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica." Molecules 17, no. 8: 8955-8967.

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