Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 21, Pages 5385-5388Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402034
Keywords
asymmetric catalysis; hydrogenation; iridium; N; Pligands; synthetic methods
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Funding
- Swiss National Science Foundation
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Asymmetric hydrogenation of maleic and fumaric acid derivatives with iridium catalysts based on N,Pligands 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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