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Synlett 2009(3): 461-465  
DOI: 10.1055/s-0028-1087532
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Diastereoselective Hydrogenation of Furan-2-carboxylic Acid Derivatives on Heterogeneous Catalysts

Michael Sebeka, Jens Holzb, Armin Börner*b,c, Klaus Jähnisch*a
a Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Richard-Willstätter-Str. 12, 12489 Berlin, Germany
Fax: +49 (30)63924454; e-Mail: klaus.jaehnisch@catalysis.de;
b Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
e-Mail: armin.boerner@catalysis.de;
c Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Further Information

Publication History

Received 1 October 2008
Publication Date:
21 January 2009 (online)

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Abstract

The heterogeneously catalyzed diastereoselective hydrogenation of furan-2-carboxylic acid derivatives modified with chiral auxiliaries is described. Chiral auxiliaries, catalysts, solvents, and additives were optimized for the reaction. Finally, the hydrogenation of furan-2-yl-[(S)-2-(hydroxydiphenylmethyl)-pyrrolidin-1-yl]-methanone resulted in a high diastereoselectivity. Removal of the auxiliary gave the tetrahydrofuran-2-carboxylic acid in 95% ee.

Key words

heterogeneous catalysis - stereoselective hydrogenation - furans - heterocycle - chiral auxiliary

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