Issue 99, 2014

Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis

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

Supplementary files

Article information

Article type
Communication
Submitted
08 Aug 2014
Accepted
17 Sep 2014
First published
24 Sep 2014
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 15669-15672

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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