One-Step Synthesis of Chiral Azamacrocycles via Palladium-Catalyzed Enantioselective Amination of 1,5-Dichloroanthraquinone and 1,5-Dichloroanthracene
Asymmetric amination of 1,5‐dichloroanthraquinone and 1,5‐dichloroanthracene with di‐ and trioxadiamines catalyzed by palladium complexes with various chiral phosphine ligands gave chiral macrocycles with ee values of up to 60%. The dependence of the chemical yields and enantiomeric excess on the na...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2010-09, Vol.352 (13), p.2299-2305 |
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| creator | Ranyuk, Elena R. Averin, Alexei D. Beletskaya, Irina P. |
| description | Asymmetric amination of 1,5‐dichloroanthraquinone and 1,5‐dichloroanthracene with di‐ and trioxadiamines catalyzed by palladium complexes with various chiral phosphine ligands gave chiral macrocycles with ee values of up to 60%. The dependence of the chemical yields and enantiomeric excess on the nature of the starting compounds and the phosphine ligands employed was demonstrated. An unexpected spontaneous resolution upon crystallization of the macrocycle comprising anthraquinone and dioxadiamine moieties was observed while in the case of the macrocycle with a trioxadiamine linker racemic monocrystals were obtained. Crystallization of the enantiomerically enriched mixtures afforded chiral macrocycles with 88–99% ee. |
| doi_str_mv | 10.1002/adsc.201000181 |
| format | Article |
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The dependence of the chemical yields and enantiomeric excess on the nature of the starting compounds and the phosphine ligands employed was demonstrated. An unexpected spontaneous resolution upon crystallization of the macrocycle comprising anthraquinone and dioxadiamine moieties was observed while in the case of the macrocycle with a trioxadiamine linker racemic monocrystals were obtained. Crystallization of the enantiomerically enriched mixtures afforded chiral macrocycles with 88–99% ee.</description><identifier>ISSN: 1615-4150</identifier><identifier>ISSN: 1615-4169</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201000181</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>amination ; Anthraquinones ; Asymmetry ; Catalysis ; Crystallization ; enantioselectivity ; homogeneous catalysis ; Ligands ; macrocycles ; Phosphines ; Spontaneous ; spontaneous resolution ; Synthesis</subject><ispartof>Advanced synthesis & catalysis, 2010-09, Vol.352 (13), p.2299-2305</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. 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Synth. Catal</addtitle><description>Asymmetric amination of 1,5‐dichloroanthraquinone and 1,5‐dichloroanthracene with di‐ and trioxadiamines catalyzed by palladium complexes with various chiral phosphine ligands gave chiral macrocycles with ee values of up to 60%. The dependence of the chemical yields and enantiomeric excess on the nature of the starting compounds and the phosphine ligands employed was demonstrated. An unexpected spontaneous resolution upon crystallization of the macrocycle comprising anthraquinone and dioxadiamine moieties was observed while in the case of the macrocycle with a trioxadiamine linker racemic monocrystals were obtained. Crystallization of the enantiomerically enriched mixtures afforded chiral macrocycles with 88–99% ee.</description><subject>amination</subject><subject>Anthraquinones</subject><subject>Asymmetry</subject><subject>Catalysis</subject><subject>Crystallization</subject><subject>enantioselectivity</subject><subject>homogeneous catalysis</subject><subject>Ligands</subject><subject>macrocycles</subject><subject>Phosphines</subject><subject>Spontaneous</subject><subject>spontaneous resolution</subject><subject>Synthesis</subject><issn>1615-4150</issn><issn>1615-4169</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkU1vEzEQhleISpTClbOPHNjgj107e4y2HyBVLVJakZvlzI4Vg9eb2puW7Q_h9-IoKOKA1NOMxs8zkuctig-Mzhil_LPpEsw4zT1lc_aqOGWS1WXFZPP62Nf0TfE2pR8ZUXOlTovftwHL5YhbspzCuMHkEhksaTcuGk8Wz6Y3EAeYwGMij86Qb8Z707ldX7ZmNH56xo5cBBNGNyT0CKN7RLLoXTB5Eva72Ke6PHew8UMcMreJ5mHnwhCQmND95xUw4LvixBqf8P3felbcX17ctV_K69urr-3iuoSKS1YK3nAhVQVrNExYydha1FhT6KARwC0ooIxLLhA6ypWU1lpscM1rVdl5BeKs-HjYu43Dww7TqHuXAPMXAw67pBkVjDdVPm9GZwc03yOliFZvo-tNnDKk9wHofQD6GEAWmoPw5DxOL9B6cb5s_3XLg-vSiL-Orok_tVRC1fr7zZVerS5XlbhptRJ_AGsgm5E</recordid><startdate>20100910</startdate><enddate>20100910</enddate><creator>Ranyuk, Elena R.</creator><creator>Averin, Alexei D.</creator><creator>Beletskaya, Irina P.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20100910</creationdate><title>One-Step Synthesis of Chiral Azamacrocycles via Palladium-Catalyzed Enantioselective Amination of 1,5-Dichloroanthraquinone and 1,5-Dichloroanthracene</title><author>Ranyuk, Elena R. ; Averin, Alexei D. ; Beletskaya, Irina P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4261-32923674cbea13f611b35e50cdc93c2fc7c012623ecd02766fffe9eb2574f84c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>amination</topic><topic>Anthraquinones</topic><topic>Asymmetry</topic><topic>Catalysis</topic><topic>Crystallization</topic><topic>enantioselectivity</topic><topic>homogeneous catalysis</topic><topic>Ligands</topic><topic>macrocycles</topic><topic>Phosphines</topic><topic>Spontaneous</topic><topic>spontaneous resolution</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ranyuk, Elena R.</creatorcontrib><creatorcontrib>Averin, Alexei D.</creatorcontrib><creatorcontrib>Beletskaya, Irina P.</creatorcontrib><collection>Istex</collection><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>Ranyuk, Elena R.</au><au>Averin, Alexei D.</au><au>Beletskaya, Irina P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-Step Synthesis of Chiral Azamacrocycles via Palladium-Catalyzed Enantioselective Amination of 1,5-Dichloroanthraquinone and 1,5-Dichloroanthracene</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2010-09-10</date><risdate>2010</risdate><volume>352</volume><issue>13</issue><spage>2299</spage><epage>2305</epage><pages>2299-2305</pages><issn>1615-4150</issn><issn>1615-4169</issn><eissn>1615-4169</eissn><abstract>Asymmetric amination of 1,5‐dichloroanthraquinone and 1,5‐dichloroanthracene with di‐ and trioxadiamines catalyzed by palladium complexes with various chiral phosphine ligands gave chiral macrocycles with ee values of up to 60%. The dependence of the chemical yields and enantiomeric excess on the nature of the starting compounds and the phosphine ligands employed was demonstrated. An unexpected spontaneous resolution upon crystallization of the macrocycle comprising anthraquinone and dioxadiamine moieties was observed while in the case of the macrocycle with a trioxadiamine linker racemic monocrystals were obtained. Crystallization of the enantiomerically enriched mixtures afforded chiral macrocycles with 88–99% ee.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201000181</doi><tpages>7</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | amination Anthraquinones Asymmetry Catalysis Crystallization enantioselectivity homogeneous catalysis Ligands macrocycles Phosphines Spontaneous spontaneous resolution Synthesis |
| title | One-Step Synthesis of Chiral Azamacrocycles via Palladium-Catalyzed Enantioselective Amination of 1,5-Dichloroanthraquinone and 1,5-Dichloroanthracene |
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