Molecules (Jul 2012)
Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from <em>Candida antarctica</em>
Abstract
The lipase B from <em>Candida antarctica</em> (Novozym 435<sup>®</sup>, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (<strong>1</strong>), (±)-5-methylhexan-2-ol (<strong>3</strong>), (±)-octan-2-ol (<strong>4</strong>), (±)-heptan-3-ol (<strong>5</strong>) and (±)-oct-1-en-3-ol (<strong>6</strong>). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% <em>ee</em>) and acetates (>99% <em>ee</em>) with good yields. Kinetic resolution of <em>rac</em>-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.
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