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^®, 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.

Keywords

• kinetic&lt;em&gt; &lt;/em&gt;resolution
• lipase
• &lt;em&gt;Candida antarctica&lt;/em&gt;
• aliphatic secondary alcohols