| Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids. | |
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MedLine Citation:
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PMID: 20701319 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A challenging direct asymmetric hydrogenation of (E)-2-oxo-4-arylbut-3-enoic acids to give 2-hydroxy-4-arylbutanoic acids (85.4-91.8% ee) was achieved with a Ru catalyst based on SunPhos as the chiral ligand. Further investigation of the reaction revealed that partial isomerization of 2-hydroxy-4-arylbutenoic acids was involved in the hydrogenation process. Employing the reaction conditions to the hydrogenation of 2-oxo-4-phenylbutanoic acid resulted in better enantioselectivity (91.8% ee) and efficiency (TON = 2000, TOF = 200 h(-1)), which offers a useful method for the synthesis of a common intermediate for ACE inhibitors. |
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Authors:
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Lvfeng Zhu; Qinghua Meng; Weizheng Fan; Xiaomin Xie; Zhaoguo Zhang |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Sep |
Date Detail:
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Created Date: 2010-08-27 Completed Date: 2010-12-08 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 6027-30 Citation Subset: IM |
Affiliation:
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School of Chemical Engineering, Nanjing University of Science & Technology, 200 Xiaolingwei, Nanjing 210094, China. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Butyric Acids
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chemical synthesis*,
chemistry Hydrogenation Molecular Structure Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Butyric Acids; 625-38-7/3-butenoic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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