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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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Supplementary files

Article information


Submitted
08 Aug 2014
Accepted
17 Sep 2014
First published
24 Sep 2014

This article is Open Access

Chem. Commun., 2014,50, 15669-15672
Article type
Communication
Author version available

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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