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Synlett 2001; 2001(1): 0111-0113
DOI: 10.1055/s-2001-9703
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Chemo-Enzymatic Enantioconvergent Synthesis of C4-Building Blocks Containing a Fully Substituted Chiral Carbon Center using Bacterial Epoxide Hydrolases

Andreas Steinreiber* , Helena Hellström, Sandra F. Mayer, Romano V. A. Orru, Kurt Faber
  • *University of Graz, Department of Chemistry, Organic and Bio-organic Chemistry, Heinrichstrasse 28, A-8010 Graz, Austria; Fax +43-316-380-9840; E-mail: kurt.faber@kfunigraz.ac.at
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Publication Date:
31 December 2001 (online)

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A highly efficient chemo-enzymatic asymmetric synthesis of chiral C4-building blocks containing a fully substituted carbon center is reported. The key transformation consists of a deracemization based on an enantioconvergent asymmetric hydrolysis of an epoxide using combined bio- and chemo-catalysis leading to a single enantiomeric product in >98% e. e. A simple switch of steps leads to kinetic resolution giving access to products of opposite configuration.

biotransformation - epoxide hydrolase - deracemization - C4-building block - enantioconvergent

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