Enzymatic resolution of rac-1,1-dimethyl-1-sila-cyclohexan-2-ol by ester hydrolysis or transesterification using a crude lipase preparation of Candida cylindracea |
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Authors: | Kirsten Fritsche Christoph Syldatk Fritz Wagner Heidi Hengelsberg Reinhold Tacke |
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Institution: | (1) Institut für Biochemie und Biotechnologie, Technische Universität Braunschweig, Konstantin-Uhde-Strasse 5, D-3300 Braunschweig, Germany;(2) Institut für Anorganische Chemie, Universität Karlsruhe, Engesserstrasse, D-7500 Karlsruhe, Germany |
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Abstract: | Summary
rac-2-Acetoxy-1,1-dimethyl-1-sila-cyclohexane (rac-2) was synthesized by esterification of rac-1,1-dimethyl-1-sila-cyclohexan-2-ol (rac-1) with acetic anhydride. Enantioselective hydrolysis of rac-2 in aqueous solution, catalysed by a crude lipase preparation of Candida cylindracea (EC 3.1.1.3), led to the formation of (S)-1 (95% ee). Enantioselective transesterification of rac-1 with triacetin in isooctane, catalysed by the same enzyme preparation, yielded (S)-2 (95% ee), which was separated by chromatography from non-reacted (R)-1 (96% ee). Recrystallization led to an improvement of the enantiomeric purity of (R)-1 and (S)-1 up to >98% ee. Thus the enantiomers of rac-1 were prepared (100 mg scale) with high enantiomeric purities by the use of two different types of enzyme-catalysed reaction. |
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