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DOI: 10.1055/s-0034-1378417
Asymmetric Hydrogenation of Maleic Acid Diesters by Iridium Catalysis
Publication History
Publication Date:
18 July 2014 (online)
Significance
In the presence of a chiral iridium complex based on a N,P-ligand system, maleic and fumaric acid derivatives undergo catalytic asymmetric hydrogenation, leading to the corresponding succinates with excellent yields and enantioselectivities. The products are important building blocks found in many bioactive compounds, for example, metalloproteinase inhibitors.
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Comment
A new class of bidentate N,P-ligands based on pyridine–phosphinites is introduced. The presence of fluoro substituents at the ortho positions of the desired ligand prevents the C–H insertion process of the iridium atom known for 2-phenylpyridines. The present method also provides asymmetric hydrogenation of cis/trans mixtures of the substrates in an enantioconvergent fashion.
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