Issue 30, 2008
From the journal:

Chemical Communications

Stereocontrolled synthesis of fully functionalized d-glucosamine monosaccharidesvia a domino nitro-Michael/Henry reaction†

Alexander Adibekian,a   Mattie S. M. Timmer,a   Pierre Stallforth,a   Jimmy van Rijn,a   Daniel B. Werzab  and  Peter H. Seeberger*a  

* Corresponding authors

a Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli-Str. 10, Zürich 8093, Switzerland
E-mail: seeberger@org.chem.ethz.ch
Fax: +41 44 633 12 35
Tel: +41 44 633 21 03

b Institute for Organic and Biomolecular Chemistry, University of Göttingen, Tammannstr. 2, 37077 Göttingen, Germany

Abstract

A diastereoselective domino nitro-Michael/Henry reaction involving a β-hydroxyaldehyde and a nitroalkene provides direct access to fully functionalized D-glucosamine monosaccharides.

Graphical abstract: Stereocontrolled synthesis of fully functionalized d-glucosamine monosaccharidesvia a domino nitro-Michael/Henry reaction

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Article information

DOI
https://doi.org/10.1039/B805159C
Article type
Communication
Submitted
27 Mar 2008
Accepted
24 Apr 2008
First published
04 Jun 2008

Chem. Commun., 2008, 3549-3551

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Stereocontrolled synthesis of fully functionalized D-glucosamine monosaccharidesvia a domino nitro-Michael/Henry reaction

A. Adibekian, M. S. M. Timmer, P. Stallforth, J. van Rijn, D. B. Werz and P. H. Seeberger, Chem. Commun., 2008, 3549 DOI: 10.1039/B805159C

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