ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A concise synthesis of enantiomerically pure aroyl-L-alanines and dihydroaroyl-L-alanines

Mária Gardiánová, Ľuboš Slížik, Anna Koreňová, František Považanec, and Dušan Berkeš

Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia

E-mail: dusan.berkes@stuba.sk

Abstract: Straightforward preparation of enantiomerically highly enriched N-substituted aroylalanines has been developed. This process involves the combination of crystallization-induced asymmetric transformation and a conjugate addition of N-nucleophiles to the corresponding aroylacrylic acids. Further transformations to 3,4-dichlorobenzoylalanine and aroyl-l-alanines via periodate oxidation and stereoselective reduction to N-substituted syn-4-aryl-4-hydroxy-2-aminobutanoic acids are also described.

Keywords: crystallization-induced asymmetric transformation – periodate degradation – aroylalanine – amino acid

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-012-0246-z

Chemical Papers 67 (1) 92–100 (2013)