Asymmetric Hydrogenation of Maleic Acid Diesters and Anhydrides |
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Authors: | Dr. Maurizio Bernasconi Marc‐André Müller Prof. Dr. Andreas Pfaltz |
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Affiliation: | University of Basel, Department of Chemistry, St. Johanns‐Ring 19, 4056 Basel (Switzerland) |
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Abstract: | Asymmetric hydrogenation of maleic and fumaric acid derivatives with iridium catalysts based on N,P ligands provides an efficient route to chiral enantioenriched succinates. A new catalyst derived from a 2,6‐difluorophenyl‐substituted pyridine‐phosphinite ligand was developed and enables the conversion of a wide range of 2‐alkyl and 2‐arylmaleic acid diesters into the corresponding succinates in high enantiomeric purity. Mixtures of cis/trans substrates can be hydrogenated in an enantioconvergent fashion with high enantioselectivity, and further enhances the scope of this transformation. The products are valuable chiral building blocks with a structural motif found in many bioactive compounds, such as metalloproteinase inhibitors. |
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Keywords: | asymmetric catalysis hydrogenation iridium N,P ligands synthetic methods |
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