Issue 1, 2007
From the journal:

Organic & Biomolecular Chemistry

CIAT with simultaneous epimerization at two stereocenters. Synthesis of substituted β-methyl-α-homophenylalanines†

Dušan Berkeš,*a   Pavol Jakubec,a   Dagmar Winklerová,a   František Považaneca  and  Adam Daich*b  

* Corresponding authors

a Department of organic chemistry, Slovak University of Technology, Radlinského 9, Bratislava, Slovakia
E-mail: dusan.berkes@stuba.sk
Fax: +421 2 52968560
Tel: +421 2 52968560

b Laboratoire de Chimie, URCOM, UFR des Techniques de l'Université du Havre, 25, rue Philippe Lebon, B.P.: 540, F-76058, Le Havre Cedex, France
E-mail: adam.daich@univ-lehavre.fr
Fax: +33 02-32-74-43-91
Tel: +33 02-32-74-44-03

Abstract

Diastereoselective aza-Michael additions of phenylethylamine to 3-aroylbutenoic acids are reported. During these processes, efficient control over two new stereogenic centers on the Michael acceptor has been possible via crystallization-induced asymmetric transformation (CIAT). As an application, a convenient two-step synthesis of anti-β-methylhomophenylalanines is also described.

Graphical abstract: CIAT with simultaneous epimerization at two stereocenters. Synthesis of substituted β-methyl-α-homophenylalanines

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Article information

DOI
https://doi.org/10.1039/B613103D
Article type
Paper
Submitted
11 Sep 2006
Accepted
31 Oct 2006
First published
23 Nov 2006

Org. Biomol. Chem., 2007,5, 121-124

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CIAT with simultaneous epimerization at two stereocenters. Synthesis of substituted β-methyl-α-homophenylalanines

D. Berkeš, P. Jakubec, D. Winklerová, F. Považanec and A. Daich, Org. Biomol. Chem., 2007, 5, 121 DOI: 10.1039/B613103D

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