Direct Asymmetric Hydrogenation of 2-Oxo-4-arylbut-3-enoic Acids

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-ar...

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Veröffentlicht in:	Journal of organic chemistry 2010-09, Vol.75 (17), p.6027-6030
Hauptverfasser:	Zhu, Lvfeng, Meng, Qinghua, Fan, Weizheng, Xie, Xiaomin, Zhang, Zhaoguo
Format:	Artikel
Sprache:	eng
Schlagworte:	Aliphatic compounds Butyrates - chemical synthesis Butyrates - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Hydrogenation Molecular Structure Organic chemistry Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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container_issue	17
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container_title	Journal of organic chemistry
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creator	Zhu, Lvfeng Meng, Qinghua Fan, Weizheng Xie, Xiaomin Zhang, Zhaoguo
description	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.
doi_str_mv	10.1021/jo101084t
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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.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo101084t</identifier><identifier>PMID: 20701319</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Butyrates - chemical synthesis ; Butyrates - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Hydrogenation ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Stereoisomerism ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>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.</description><subject>Aliphatic compounds</subject><subject>Butyrates - chemical synthesis</subject><subject>Butyrates - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Hydrogenation</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Theory of reactions, general kinetics. Catalysis. 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Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Lvfeng</creatorcontrib><creatorcontrib>Meng, Qinghua</creatorcontrib><creatorcontrib>Fan, Weizheng</creatorcontrib><creatorcontrib>Xie, Xiaomin</creatorcontrib><creatorcontrib>Zhang, Zhaoguo</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Lvfeng</au><au>Meng, Qinghua</au><au>Fan, Weizheng</au><au>Xie, Xiaomin</au><au>Zhang, Zhaoguo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Asymmetric Hydrogenation of 2-Oxo-4-arylbut-3-enoic Acids</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2010-09-03</date><risdate>2010</risdate><volume>75</volume><issue>17</issue><spage>6027</spage><epage>6030</epage><pages>6027-6030</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>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.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20701319</pmid><doi>10.1021/jo101084t</doi><tpages>4</tpages></addata></record>
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subjects	Aliphatic compounds Butyrates - chemical synthesis Butyrates - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Hydrogenation Molecular Structure Organic chemistry Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
title	Direct Asymmetric Hydrogenation of 2-Oxo-4-arylbut-3-enoic Acids
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