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

M Sebek, J Holz, A Börner, K Jähnisch

Index: Sebek, Michael; Holz, Jens; Boerner, Armin; Jaehnisch, Klaus Synlett, 2009 , # 3 p. 461 - 465

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Citation Number: 9

Abstract

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 ...