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

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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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