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

Lipase-Catalyzed Kinetic Resolution of Aryltrimethylsilyl Chiral Alcohols

Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, n°. 748, SP 05508-900, São Paulo, Brazil
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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
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MDPI and ACS Style

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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