Asymmetric Hydrogenation of Maleic Acid Diesters and Anhydrides**

被引:30
作者
Bernasconi, Maurizio [1 ]
Mueller, Marc-Andre [1 ]
Pfaltz, Andreas [1 ]
机构
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
基金
瑞士国家科学基金会;
关键词
asymmetric catalysis; hydrogenation; iridium; N; Pligands; synthetic methods; CATALYZED ENANTIOSELECTIVE HYDROGENATION; MATRIX-METALLOPROTEINASE INHIBITORS; CARBONYL-COMPOUNDS; EFFICIENT LIGANDS; IRIDIUM CATALYSTS; ARYLBORONIC ACIDS; ITACONIC ACID; COMPLEXES; OLEFINS; DERIVATIVES;
D O I
10.1002/anie.201402034
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:5385 / 5388
页数:4
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