Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand
The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2‐((2R,5R)‐2,5‐dimethyl‐phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-04, Vol.361 (8), p.1913-1920 |
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| container_end_page | 1920 |
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| container_issue | 8 |
| container_start_page | 1913 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 361 |
| creator | Garbe, Marcel Wei, Zhihong Tannert, Bianca Spannenberg, Anke Jiao, Haijun Bachmann, Stephan Scalone, Michelangelo Junge, Kathrin Beller, Matthias |
| description | The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2‐((2R,5R)‐2,5‐dimethyl‐phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non‐noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity. |
| doi_str_mv | 10.1002/adsc.201801511 |
| format | Article |
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The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non‐noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201801511</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Aliphatic compounds ; Asymmetric Catalysis ; Asymmetric Hydrogenation ; Chiral Alcohols ; Chiral Pincer ; Coordination compounds ; Enantiomers ; Iron ; Ketones ; Ligands ; Manganese ; Noble metals ; Prochiral Ketones ; Selectivity ; Substrates</subject><ispartof>Advanced synthesis & catalysis, 2019-04, Vol.361 (8), p.1913-1920</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. 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The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non‐noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity.</description><subject>Aliphatic compounds</subject><subject>Asymmetric Catalysis</subject><subject>Asymmetric Hydrogenation</subject><subject>Chiral Alcohols</subject><subject>Chiral Pincer</subject><subject>Coordination compounds</subject><subject>Enantiomers</subject><subject>Iron</subject><subject>Ketones</subject><subject>Ligands</subject><subject>Manganese</subject><subject>Noble metals</subject><subject>Prochiral Ketones</subject><subject>Selectivity</subject><subject>Substrates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkEFPAjEQhRujiYhePTfxDLbbdpc9kgXFiEqinpvSTqFkabFdRP69SzB69DSTN-_NSz6ErinpU0KyW2WS7meEDggVlJ6gDs2p6HGal6e_uyDn6CKlFSG0GBRFB7mxV75xIUENunGfgCd7E8MCvGpVj4PFj9AEDwlvk_MLPHLWQgTf4CdoVI2rsN7U8NXed65ZYoWrpYutPnue4ZnzGiKeuoXy5hKdWVUnuPqZXfR-N36rJr3py_1DNZz2NBOc9nKWK0NMYeaUmExzWypqOGdCD0qa63kpjCWWZYwbkoscLC8VZ4opC8xSRlgX3Rz_bmL42EJq5Cpso28rZZa1oERRsqJ19Y8uHUNKEazcRLdWcS8pkQec8oBT_uJsA-UxsHM17P9xy-HotfrLfgPG8nmR</recordid><startdate>20190416</startdate><enddate>20190416</enddate><creator>Garbe, Marcel</creator><creator>Wei, Zhihong</creator><creator>Tannert, Bianca</creator><creator>Spannenberg, Anke</creator><creator>Jiao, Haijun</creator><creator>Bachmann, Stephan</creator><creator>Scalone, Michelangelo</creator><creator>Junge, Kathrin</creator><creator>Beller, Matthias</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20190416</creationdate><title>Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand</title><author>Garbe, Marcel ; Wei, Zhihong ; Tannert, Bianca ; Spannenberg, Anke ; Jiao, Haijun ; Bachmann, Stephan ; Scalone, Michelangelo ; Junge, Kathrin ; Beller, Matthias</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3541-636ad0d7db10d2c4f9a1d4435c8916cb95df0f3234d0656ef49a43a3afe3f1303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aliphatic compounds</topic><topic>Asymmetric Catalysis</topic><topic>Asymmetric Hydrogenation</topic><topic>Chiral Alcohols</topic><topic>Chiral Pincer</topic><topic>Coordination compounds</topic><topic>Enantiomers</topic><topic>Iron</topic><topic>Ketones</topic><topic>Ligands</topic><topic>Manganese</topic><topic>Noble metals</topic><topic>Prochiral Ketones</topic><topic>Selectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Garbe, Marcel</creatorcontrib><creatorcontrib>Wei, Zhihong</creatorcontrib><creatorcontrib>Tannert, Bianca</creatorcontrib><creatorcontrib>Spannenberg, Anke</creatorcontrib><creatorcontrib>Jiao, Haijun</creatorcontrib><creatorcontrib>Bachmann, Stephan</creatorcontrib><creatorcontrib>Scalone, Michelangelo</creatorcontrib><creatorcontrib>Junge, Kathrin</creatorcontrib><creatorcontrib>Beller, Matthias</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Garbe, Marcel</au><au>Wei, Zhihong</au><au>Tannert, Bianca</au><au>Spannenberg, Anke</au><au>Jiao, Haijun</au><au>Bachmann, Stephan</au><au>Scalone, Michelangelo</au><au>Junge, Kathrin</au><au>Beller, Matthias</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2019-04-16</date><risdate>2019</risdate><volume>361</volume><issue>8</issue><spage>1913</spage><epage>1920</epage><pages>1913-1920</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2‐((2R,5R)‐2,5‐dimethyl‐phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non‐noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201801511</doi><tpages>8</tpages></addata></record> |
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| subjects | Aliphatic compounds Asymmetric Catalysis Asymmetric Hydrogenation Chiral Alcohols Chiral Pincer Coordination compounds Enantiomers Iron Ketones Ligands Manganese Noble metals Prochiral Ketones Selectivity Substrates |
| title | Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand |
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