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Enzymemimetic C-C and C-N Bond Formations

  • Conference paper
Stereoselective Synthesis

Summary

Simple C2 and C3 building blocks, such as dihydroxyacetone phosphate (DHAP), phosphoenol pyruvate (PEP) and the active acetaldehyde or glycolaldehyde, are used by nature in enzyme catalyzed, highly stereoselective C-C bond forming reactions. The first enantiopure chemical synthetic equivalents of these building blocks are synthesized and employed in enzymemimetic C-C bond formations. Stereoselective C-N bond formations can be mimicked by using a chiral ammonia equivalent in Michael additions to enoates. It turns out, that this biomimetic strategy opens a way to both enantiomers of the final products in a broad applicability and that diastereo- and enantioselectivities are reached, which compare well with the corresponding enzymatic processes.

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Authors and Affiliations

  1. Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Str. 1, D-52074, Aachen, Deutschland

    D. Enders

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  1. D. Enders
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Editors and Affiliations

  1. Schering AG Berlin, D-13342, Berlin, Germany

    Eckhard Ottow , Klaus Schöllkopf  & Bernd-Günter Schulz ,  & 

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© 1994 Springer-Verlag Berlin Heidelberg

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Enders, D. (1994). Enzymemimetic C-C and C-N Bond Formations. In: Ottow, E., Schöllkopf, K., Schulz, BG. (eds) Stereoselective Synthesis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-78496-5_4

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  • DOI: https://doi.org/10.1007/978-3-642-78496-5_4

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-78498-9

  • Online ISBN: 978-3-642-78496-5

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