Synthesis and Molecular Modeling Studies of SYNPHOS®, a New, Efficient Diphosphane Ligand For Ruthenium-Catalyzed Asymmetric Hydrogenation
A new, optically active, atropisomeric diphosphane ligand, (2,3,2′,3′‐tetrahydro‐5,5′‐bi(1,4‐benzodioxin)‐6,6′‐diyl)bis‐(diphenylphosphane) (SYNPHOS®), has been synthesized, characterized, and used in ruthenium‐catalyzed asymmetric hydrogenations. This new ligand has been compared with other atropis...
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Veröffentlicht in: | European journal of organic chemistry 2003-05, Vol.2003 (10), p.1931-1941 |
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container_issue | 10 |
container_start_page | 1931 |
container_title | European journal of organic chemistry |
container_volume | 2003 |
creator | Paule, Sébastien Duprat de Jeulin, Séverine Ratovelomanana-Vidal, Virginie Genêt, Jean-Pierre Champion, Nicolas Dellis, Philippe |
description | A new, optically active, atropisomeric diphosphane ligand, (2,3,2′,3′‐tetrahydro‐5,5′‐bi(1,4‐benzodioxin)‐6,6′‐diyl)bis‐(diphenylphosphane) (SYNPHOS®), has been synthesized, characterized, and used in ruthenium‐catalyzed asymmetric hydrogenations. This new ligand has been compared with other atropisomeric diphosphanes (BINAP and MeO‐BIPHEP) with respect to their dihedral angles calculated by molecular modeling and the enantioselectivity of their ruthenium‐mediated hydrogenation reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) |
doi_str_mv | 10.1002/ejoc.200200634 |
format | Article |
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This new ligand has been compared with other atropisomeric diphosphanes (BINAP and MeO‐BIPHEP) with respect to their dihedral angles calculated by molecular modeling and the enantioselectivity of their ruthenium‐mediated hydrogenation reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200200634</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Asymmetric catalysis ; Atropisomerism ; Hydrogenation ; Molecular modeling ; Phosphanes ; Ruthenium</subject><ispartof>European journal of organic chemistry, 2003-05, Vol.2003 (10), p.1931-1941</ispartof><rights>2002 WILEY‐VCH Verlag GmbH & Co. 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KGaA, 69451 Weinheim, Germany, 2003)</description><subject>Asymmetric catalysis</subject><subject>Atropisomerism</subject><subject>Hydrogenation</subject><subject>Molecular modeling</subject><subject>Phosphanes</subject><subject>Ruthenium</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNqFkMFOwkAURRujiYhuXc8HUJzpTAtdEkSQIBiLAd1MpjOvMFhaMlOC9Rf8Fz_CL7MEQ9y5emfxzk3udZxrgpsEY-8GVrlsehVhHFB24tQIDkMXByE-rZhR5pKQzs-dC2tXGOMwCEjN-YzKrFiC1RaJTKGHPAW5TYWpSEGqswWKiq3SYFGeoOhl_DiYRN9fDSTQGHYN1EsSLTVkBbrVm2VuN0uRARrpxT7sLjfoaVulZ3q7druiEGn5AQp1bLleQ2G0RINSmXwBmSh0nl06Z4lILVz93rrzfNebdgfuaNK_73ZGrqQhYa5SPsHKTxi0ApaQGBPhtSkjMlbAGGmrWPkxTUTVHJhk0sMyjKkXsFjIFhOC1p3mIVea3FoDCd8YvRam5ATz_ZR8PyU_TlkJ4UHY6RTKf755bzjp_nXdg6ttAe9HV5g3HrRoy-ezcZ9Ph5E3mw9feUB_AHT5is4</recordid><startdate>200305</startdate><enddate>200305</enddate><creator>Paule, Sébastien Duprat de</creator><creator>Jeulin, Séverine</creator><creator>Ratovelomanana-Vidal, Virginie</creator><creator>Genêt, Jean-Pierre</creator><creator>Champion, Nicolas</creator><creator>Dellis, Philippe</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200305</creationdate><title>Synthesis and Molecular Modeling Studies of SYNPHOS®, a New, Efficient Diphosphane Ligand For Ruthenium-Catalyzed Asymmetric Hydrogenation</title><author>Paule, Sébastien Duprat de ; Jeulin, Séverine ; Ratovelomanana-Vidal, Virginie ; Genêt, Jean-Pierre ; Champion, Nicolas ; Dellis, Philippe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3914-dd510d5f4e764f1b01a28341cbde4418dbd5b3fa069e4c4c20c9b3264bac74aa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Asymmetric catalysis</topic><topic>Atropisomerism</topic><topic>Hydrogenation</topic><topic>Molecular modeling</topic><topic>Phosphanes</topic><topic>Ruthenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Paule, Sébastien Duprat de</creatorcontrib><creatorcontrib>Jeulin, Séverine</creatorcontrib><creatorcontrib>Ratovelomanana-Vidal, Virginie</creatorcontrib><creatorcontrib>Genêt, Jean-Pierre</creatorcontrib><creatorcontrib>Champion, Nicolas</creatorcontrib><creatorcontrib>Dellis, Philippe</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Paule, Sébastien Duprat de</au><au>Jeulin, Séverine</au><au>Ratovelomanana-Vidal, Virginie</au><au>Genêt, Jean-Pierre</au><au>Champion, Nicolas</au><au>Dellis, Philippe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Molecular Modeling Studies of SYNPHOS®, a New, Efficient Diphosphane Ligand For Ruthenium-Catalyzed Asymmetric Hydrogenation</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2003-05</date><risdate>2003</risdate><volume>2003</volume><issue>10</issue><spage>1931</spage><epage>1941</epage><pages>1931-1941</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A new, optically active, atropisomeric diphosphane ligand, (2,3,2′,3′‐tetrahydro‐5,5′‐bi(1,4‐benzodioxin)‐6,6′‐diyl)bis‐(diphenylphosphane) (SYNPHOS®), has been synthesized, characterized, and used in ruthenium‐catalyzed asymmetric hydrogenations. This new ligand has been compared with other atropisomeric diphosphanes (BINAP and MeO‐BIPHEP) with respect to their dihedral angles calculated by molecular modeling and the enantioselectivity of their ruthenium‐mediated hydrogenation reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200200634</doi><tpages>11</tpages></addata></record> |
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subjects | Asymmetric catalysis Atropisomerism Hydrogenation Molecular modeling Phosphanes Ruthenium |
title | Synthesis and Molecular Modeling Studies of SYNPHOS®, a New, Efficient Diphosphane Ligand For Ruthenium-Catalyzed Asymmetric Hydrogenation |
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