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

Michael Sebek; Jens Holz; Armin Börner; Klaus Jähnisch

doi:10.1055/s-0028-1087532

LETTER

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

Michael Sebek^a, Jens Holz^b, 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

Abstract

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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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