Efficient Ru(II)-catalyzed asymmetric hydrogenation of simple ketones with C2-symmetric planar chiral metallocenyl phosphinooxazoline ligands
C2-symmetric metallocenyl planar phosphinooxazoline ligands (2 and 3) have been applied in the Ru(II)-catalyzed asymmetric hydrogenation of simple ketones. This type of ligands enjoys the advantages of dual reaction sites as well as larger steric hindrance than their corresponding C1-symmetric count...
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| Veröffentlicht in: | Tetrahedron 2012-04, Vol.68 (16), p.3295-3299 |
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| creator | Guo, Hui Liu, Delong Butt, Nicholas A. Liu, Yangang Zhang, Wanbin |
| description | C2-symmetric metallocenyl planar phosphinooxazoline ligands (2 and 3) have been applied in the Ru(II)-catalyzed asymmetric hydrogenation of simple ketones. This type of ligands enjoys the advantages of dual reaction sites as well as larger steric hindrance than their corresponding C1-symmetric counterparts. As a result, almost quantitative conversions and excellent enantioselectivities were obtained for a series of simple ketones. Under the optimal reaction conditions, up to 99.7% ee was obtained in many cases. It was also confirmed that hydrogen rather than reaction solvent i-PrOH is at work in the hydrogenation procedure.
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| doi_str_mv | 10.1016/j.tet.2012.02.075 |
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[Display omitted]</description><subject>Asymmetry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Conversion</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Hydrogenation</subject><subject>Ketone</subject><subject>Ketones</subject><subject>Ligands</subject><subject>Optimization</subject><subject>Organic chemistry</subject><subject>Phosphinooxazoline ligands</subject><subject>Planar chirality</subject><subject>Preparations and properties</subject><subject>Ru-catalyzed asymmetric hydrogenation</subject><subject>Solvents</subject><subject>Tetrahedrons</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9UcGKFDEQbUTBcfUDvOUirIceK5mkexpPMqw6sCCInkNNurKdMZ20SUbt_Qf_2R5m0ZvwoKB471XVq6p6yWHNgTdvjutCZS2AizUsaNWjasVlI2slefO4WgFIqCUIeFo9y_kIAJyLzar6fWOtM45CYZ9P1_v969pgQT_fU88wz-NIJTnDhrlP8Y4CFhcDi5ZlN06e2DcqMVBmP10Z2E7U_xSTx4CJmcEl9GxpovfRUJg9m4aYp8GFGH_hffQuEPPuDkOfn1dPLPpMLx7qVfX1_c2X3cf69tOH_e7dbW0EKF6b1jTQHrZEcqOM4IdeIe_sAQWZrpPqoLDj_VbIjixJTp21tlMoUYiO0xY3V9X1xXdK8fuJctGjy4b8sjPFU9a8lbLZCgV8ofIL1aSYcyKrp-RGTLPmoM_R66Neotfn6DUsaNWiefVgj9mgtwmDcfmvUKhWwEbBwnt74dFy6w9HSefzKwz1LpEpuo_uP1P-ANLcnP8</recordid><startdate>20120422</startdate><enddate>20120422</enddate><creator>Guo, Hui</creator><creator>Liu, Delong</creator><creator>Butt, Nicholas A.</creator><creator>Liu, Yangang</creator><creator>Zhang, Wanbin</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120422</creationdate><title>Efficient Ru(II)-catalyzed asymmetric hydrogenation of simple ketones with C2-symmetric planar chiral metallocenyl phosphinooxazoline ligands</title><author>Guo, Hui ; Liu, Delong ; Butt, Nicholas A. ; Liu, Yangang ; Zhang, Wanbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2051-c7c607b8ee435c21bd5a19fba2ec9945b5a91d8249efe41e9fff95a4a2291e8a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Asymmetry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Conversion</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Hydrogenation</topic><topic>Ketone</topic><topic>Ketones</topic><topic>Ligands</topic><topic>Optimization</topic><topic>Organic chemistry</topic><topic>Phosphinooxazoline ligands</topic><topic>Planar chirality</topic><topic>Preparations and properties</topic><topic>Ru-catalyzed asymmetric hydrogenation</topic><topic>Solvents</topic><topic>Tetrahedrons</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guo, Hui</creatorcontrib><creatorcontrib>Liu, Delong</creatorcontrib><creatorcontrib>Butt, Nicholas A.</creatorcontrib><creatorcontrib>Liu, Yangang</creatorcontrib><creatorcontrib>Zhang, Wanbin</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guo, Hui</au><au>Liu, Delong</au><au>Butt, Nicholas A.</au><au>Liu, Yangang</au><au>Zhang, Wanbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Ru(II)-catalyzed asymmetric hydrogenation of simple ketones with C2-symmetric planar chiral metallocenyl phosphinooxazoline ligands</atitle><jtitle>Tetrahedron</jtitle><date>2012-04-22</date><risdate>2012</risdate><volume>68</volume><issue>16</issue><spage>3295</spage><epage>3299</epage><pages>3295-3299</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>C2-symmetric metallocenyl planar phosphinooxazoline ligands (2 and 3) have been applied in the Ru(II)-catalyzed asymmetric hydrogenation of simple ketones. This type of ligands enjoys the advantages of dual reaction sites as well as larger steric hindrance than their corresponding C1-symmetric counterparts. As a result, almost quantitative conversions and excellent enantioselectivities were obtained for a series of simple ketones. Under the optimal reaction conditions, up to 99.7% ee was obtained in many cases. It was also confirmed that hydrogen rather than reaction solvent i-PrOH is at work in the hydrogenation procedure.
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| fulltext | fulltext |
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| ispartof | Tetrahedron, 2012-04, Vol.68 (16), p.3295-3299 |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Asymmetry Catalysis Catalysts: preparations and properties Chemistry Conversion Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Hydrogenation Ketone Ketones Ligands Optimization Organic chemistry Phosphinooxazoline ligands Planar chirality Preparations and properties Ru-catalyzed asymmetric hydrogenation Solvents Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Efficient Ru(II)-catalyzed asymmetric hydrogenation of simple ketones with C2-symmetric planar chiral metallocenyl phosphinooxazoline ligands |
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