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Issue 99, 2014
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Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis

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Abstract

An efficient route for the synthesis of all four diastereomers of PMP-protected α-amino-γ-butyrolacton to access γ-hydroxynorvaline was established. The asymmetric key steps comprise an organocatalytic Mannich reaction and an enzymatic ketone reduction. Three reaction steps could be integrated in a one-pot process, using 2-PrOH both as solvent and as reducing agent. The sequential construction of stereogenic centres gave access to each of the four stereoisomers in high yield and with excellent stereocontrol.

Graphical abstract: Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis

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Publication details

The article was received on 08 Aug 2014, accepted on 17 Sep 2014 and first published on 24 Sep 2014


Article type: Communication
DOI: 10.1039/C4CC06230B
Citation: Chem. Commun., 2014,50, 15669-15672
  • Open access: Creative Commons BY license
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    Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis

    R. C. Simon, E. Busto, J. H. Schrittwieser, J. H. Sattler, J. Pietruszka, K. Faber and W. Kroutil, Chem. Commun., 2014, 50, 15669
    DOI: 10.1039/C4CC06230B

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