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Molecules 2011, 16(11), 9697-9713; doi:10.3390/molecules16119697
Article

Lipase-Catalyzed Kinetic Resolution of Aryltrimethylsilyl Chiral Alcohols

,
 and
*
Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, n°. 748, SP 05508-900, São Paulo, Brazil
* Author to whom correspondence should be addressed.
Received: 27 September 2011 / Revised: 28 October 2011 / Accepted: 17 November 2011 / Published: 23 November 2011
(This article belongs to the Special Issue Organosilicon Chemistry)
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Abstract

Lipase-catalyzed kinetic resolution of aryltrimethylsilyl chiral alcohols through a transesterification reaction was studied. The optimal conditions found for the kinetic resolution of m- and p-aryltrimethylsilyl chiral alcohols, led to excellent results, high conversions (c = 50%), high enantiomeric ratios (E > 200) and enantiomeric excesses for the remaining (S)-alcohol and (R)-acetylated product (>99%). However, kinetic resolution of o-aryltrimethylsilyl chiral alcohols did not occur under the same conditions applied to the other isomers.
Keywords: lipase; aryltrimethylsilyl chiral alcohols; kinetic resolution; transesterification lipase; aryltrimethylsilyl chiral alcohols; kinetic resolution; transesterification
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.

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Palmeira, D.J.; Abreu, J.C.; Andrade, L.H. Lipase-Catalyzed Kinetic Resolution of Aryltrimethylsilyl Chiral Alcohols. Molecules 2011, 16, 9697-9713.

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