Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines
Suitably substituted enantioenriched 4‐aryl‐1,4‐dihydro‐pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4‐arylpyridines with central‐to‐axial chirality conversion. Moderate to complete percentages (cp) were observed, and a model...
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| Veröffentlicht in: | Angewandte Chemie 2016-01, Vol.128 (4), p.1423-1427 |
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| container_title | Angewandte Chemie |
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| creator | Quinonero, Ophélie Jean, Marion Vanthuyne, Nicolas Roussel, Christian Bonne, Damien Constantieux, Thierry Bressy, Cyril Bugaut, Xavier Rodriguez, Jean |
| description | Suitably substituted enantioenriched 4‐aryl‐1,4‐dihydro‐pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4‐arylpyridines with central‐to‐axial chirality conversion. Moderate to complete percentages (cp) were observed, and a model for the conversion of chirality is discussed.
Enantiomerenangereicherte 4‐Aryl‐1,4‐dihydropyridin‐Derivate sind durch eine enantioselektive Michael‐Addition zugänglich. Anschließende Oxidation mit MnO2 überführt sie in axial‐chirale 4‐Arylpyridine. Diese Chiralitätsumwandlung verläuft in mäßiger bis vollständiger Weise. Ein Modell für den Prozess wird diskutiert. |
| doi_str_mv | 10.1002/ange.201509967 |
| format | Article |
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Enantiomerenangereicherte 4‐Aryl‐1,4‐dihydropyridin‐Derivate sind durch eine enantioselektive Michael‐Addition zugänglich. Anschließende Oxidation mit MnO2 überführt sie in axial‐chirale 4‐Arylpyridine. Diese Chiralitätsumwandlung verläuft in mäßiger bis vollständiger Weise. Ein Modell für den Prozess wird diskutiert.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201509967</identifier><language>eng ; ger</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Aromatic compounds ; Atropisomere ; Chemistry ; Chirality ; Chiralitätsumwandlung ; Conversion ; Enantiomers ; Enantioselektivität ; Organokatalyse ; Pyridine ; Pyridines ; Synthesis</subject><ispartof>Angewandte Chemie, 2016-01, Vol.128 (4), p.1423-1427</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2617-edefd2e65404834c38b6f2627c4d3f8805bd42abe26dba94608ece86f19418fa3</citedby><cites>FETCH-LOGICAL-c2617-edefd2e65404834c38b6f2627c4d3f8805bd42abe26dba94608ece86f19418fa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201509967$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201509967$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Quinonero, Ophélie</creatorcontrib><creatorcontrib>Jean, Marion</creatorcontrib><creatorcontrib>Vanthuyne, Nicolas</creatorcontrib><creatorcontrib>Roussel, Christian</creatorcontrib><creatorcontrib>Bonne, Damien</creatorcontrib><creatorcontrib>Constantieux, Thierry</creatorcontrib><creatorcontrib>Bressy, Cyril</creatorcontrib><creatorcontrib>Bugaut, Xavier</creatorcontrib><creatorcontrib>Rodriguez, Jean</creatorcontrib><title>Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>Suitably substituted enantioenriched 4‐aryl‐1,4‐dihydro‐pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4‐arylpyridines with central‐to‐axial chirality conversion. Moderate to complete percentages (cp) were observed, and a model for the conversion of chirality is discussed.
Enantiomerenangereicherte 4‐Aryl‐1,4‐dihydropyridin‐Derivate sind durch eine enantioselektive Michael‐Addition zugänglich. Anschließende Oxidation mit MnO2 überführt sie in axial‐chirale 4‐Arylpyridine. Diese Chiralitätsumwandlung verläuft in mäßiger bis vollständiger Weise. Ein Modell für den Prozess wird diskutiert.</description><subject>Aromatic compounds</subject><subject>Atropisomere</subject><subject>Chemistry</subject><subject>Chirality</subject><subject>Chiralitätsumwandlung</subject><subject>Conversion</subject><subject>Enantiomers</subject><subject>Enantioselektivität</subject><subject>Organokatalyse</subject><subject>Pyridine</subject><subject>Pyridines</subject><subject>Synthesis</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkUtv1DAUhSMEEkNhyzoSGzYebMfxg10UdaZIfaiiiKXlJDczLhk72J626YqfTkZTVYgFrKwrf-fo3nOy7D3BS4Ix_WTcBpYUkxIrxcWLbEFKSlAhSvEyW2DMGJKUqdfZmxhvMcacCrXIftV-11hn3Sa_ChvjfGuSGaZoY35v0zavwaVgBpQ8qh6sGfJ6a-fZpimvvbuDEK13n_MqBT_6CAO0yd5BfmZceoztFt1MI-RfJ5e2cPD0fc5QFaZhnILtrIP4NnvVmyHCu6f3JPu2Or2pz9D51fpLXZ2jlnIiEHTQdxR4yTCTBWsL2fCezje0rCt6KXHZdIyaBijvGqMYxxJakLwnihHZm-Ik-3j0HYP_uYeY9M7GFobBOPD7qImcI1JUFWRGP_yF3vp9cPN2mqg5R8Ekl_-k5sy5EJQdvJZHqg0-xgC9HoPdmTBpgvWhNn2oTT_XNgvUUXBvB5j-Q-vqcn36pxYdtTYmeHjWmvBDz7-i1N8v1_qaXojV9UpqUfwG0ByskQ</recordid><startdate>20160122</startdate><enddate>20160122</enddate><creator>Quinonero, Ophélie</creator><creator>Jean, Marion</creator><creator>Vanthuyne, Nicolas</creator><creator>Roussel, Christian</creator><creator>Bonne, Damien</creator><creator>Constantieux, Thierry</creator><creator>Bressy, Cyril</creator><creator>Bugaut, Xavier</creator><creator>Rodriguez, Jean</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>20160122</creationdate><title>Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines</title><author>Quinonero, Ophélie ; Jean, Marion ; Vanthuyne, Nicolas ; Roussel, Christian ; Bonne, Damien ; Constantieux, Thierry ; Bressy, Cyril ; Bugaut, Xavier ; Rodriguez, Jean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2617-edefd2e65404834c38b6f2627c4d3f8805bd42abe26dba94608ece86f19418fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; ger</language><creationdate>2016</creationdate><topic>Aromatic compounds</topic><topic>Atropisomere</topic><topic>Chemistry</topic><topic>Chirality</topic><topic>Chiralitätsumwandlung</topic><topic>Conversion</topic><topic>Enantiomers</topic><topic>Enantioselektivität</topic><topic>Organokatalyse</topic><topic>Pyridine</topic><topic>Pyridines</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Quinonero, Ophélie</creatorcontrib><creatorcontrib>Jean, Marion</creatorcontrib><creatorcontrib>Vanthuyne, Nicolas</creatorcontrib><creatorcontrib>Roussel, Christian</creatorcontrib><creatorcontrib>Bonne, Damien</creatorcontrib><creatorcontrib>Constantieux, Thierry</creatorcontrib><creatorcontrib>Bressy, Cyril</creatorcontrib><creatorcontrib>Bugaut, Xavier</creatorcontrib><creatorcontrib>Rodriguez, Jean</creatorcontrib><collection>Istex</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>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Quinonero, Ophélie</au><au>Jean, Marion</au><au>Vanthuyne, Nicolas</au><au>Roussel, Christian</au><au>Bonne, Damien</au><au>Constantieux, Thierry</au><au>Bressy, Cyril</au><au>Bugaut, Xavier</au><au>Rodriguez, Jean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. 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Enantiomerenangereicherte 4‐Aryl‐1,4‐dihydropyridin‐Derivate sind durch eine enantioselektive Michael‐Addition zugänglich. Anschließende Oxidation mit MnO2 überführt sie in axial‐chirale 4‐Arylpyridine. Diese Chiralitätsumwandlung verläuft in mäßiger bis vollständiger Weise. Ein Modell für den Prozess wird diskutiert.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ange.201509967</doi><tpages>5</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aromatic compounds Atropisomere Chemistry Chirality Chiralitätsumwandlung Conversion Enantiomers Enantioselektivität Organokatalyse Pyridine Pyridines Synthesis |
| title | Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines |
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