Document Detail


Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids.
MedLine Citation:
PMID:  20701319     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Lvfeng Zhu; Qinghua Meng; Weizheng Fan; Xiaomin Xie; Zhaoguo Zhang
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Sep 
Date Detail:
Created Date:  2010-08-27     Completed Date:  2010-12-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6027-30     Citation Subset:  IM    
Affiliation:
School of Chemical Engineering, Nanjing University of Science & Technology, 200 Xiaolingwei, Nanjing 210094, China.
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MeSH Terms
Descriptor/Qualifier:
Butyric Acids / chemical synthesis*,  chemistry
Hydrogenation
Molecular Structure
Stereoisomerism
Chemical
Reg. No./Substance:
0/Butyric Acids; 625-38-7/3-butenoic acid

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