Synthesis 2013; 45(19): 2763-2767
DOI: 10.1055/s-0033-1339492
paper
© Georg Thieme Verlag Stuttgart · New York

Medium Buffer Effects on the Condensation of l-Cysteine and Aryl Nitriles to (R)-2-Aryl-4,5-dihydrothiazole-4-carboxylic Acids

Oleg V. Maltsev
Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85748 Garching bei München, Germany   Fax: +49(89)28913669   Email: lukas.hintermann@tum.de
,
Valérianne Walter
Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85748 Garching bei München, Germany   Fax: +49(89)28913669   Email: lukas.hintermann@tum.de
,
Matthias J. Brandl
Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85748 Garching bei München, Germany   Fax: +49(89)28913669   Email: lukas.hintermann@tum.de
,
Lukas Hintermann*
Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85748 Garching bei München, Germany   Fax: +49(89)28913669   Email: lukas.hintermann@tum.de
› Author Affiliations
Further Information

Publication History

Received: 02 July 2013

Accepted after revision: 11 July 2013

Publication Date:
24 July 2013 (online)


Abstract

The condensation of l-cysteine and aryl nitriles to (R)-2-aryl-4,5-dihydrothiazole-4-carboxylic acids in buffered media was reinvestigated. Pure products (yields of 58–95%; up to 99% ee) were obtained in a NaHCO3/NaOH-buffered aqueous alcoholic medium.

Supporting Information