<![CDATA[<ce:abstract xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns="http://www.elsevier.com/xml/ja/dtd" class="graphical" xml:lang="en" id="ab005" view="all"><ce:section-title id="st005">Graphical abstract</ce:section-title><ce:abstract-sec id="as005" view="all"><ce:simple-para>Display Omitted</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns="http://www.elsevier.com/xml/ja/dtd" class="author" xml:lang="en" id="ab010" view="all"><ce:section-title id="st010">Abstract</ce:section-title><ce:abstract-sec id="as010" view="all"><ce:simple-para id="sp0010" view="all">In a route towards enantiomerically enriched 1-(β-hydroxypropyl)indoles, which are potentially useful building blocks for high value-added chemicals synthesis, a kinetic resolution approach by means of lipase-catalyzed enantioselective acylation as well as hydrolysis/methanolysis has been elaborated for the first time. The enzymatic resolution of chiral<ce:italic>N</ce:italic>-substituted indole-based<ce:italic>sec</ce:italic>-alcohols was successfully accomplished, yielding both enantiomeric forms of the employed derivatives with up to >99% enantiomeric purity via an enantioselective transesterification under mild reaction conditions. The most selective resolutions were obtained using fungal (CAL-B and TLL) and bacterial (PFL and BCL) lipases and vinyl acetate as the acyl?group donor. The synthetic protocol described herein is very simple, user-friendly and efficient, thus paving the way for future access towards more complex compounds of this type. The absolute configurations of novel enantiomeric derivatives, and thus stereoselectivity of the described enzymatic reactions were confirmed by application of CDA-based NMR methodology and single-crystal X-ray diffraction analysis.</ce:simple-para></ce:abstract-sec></ce:abstract>]]>
Iwona Justyniak、Zbigniew Ochal、Pawe? Borowiecki
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Institute of Physical Chemistry, Polish Academy of Sciences
Warsaw University of Technology, Faculty of Chemistry, Department of Drugs Technology and Biotechnology
NSTL
Elsevier
