Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes
An enantioselective oxidative carbocyclization–borylation of enallenes that is catalyzed by palladium(II) and a Brønsted acid was developed. Biphenol‐type chiral phosphoric acids were superior co‐catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were s...
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| Veröffentlicht in: | Angewandte Chemie 2015-05, Vol.127 (20), p.6122-6125 |
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| creator | Jiang, Tuo Bartholomeyzik, Teresa Mazuela, Javier Willersinn, Jochen Bäckvall, Jan-E. |
| description | An enantioselective oxidative carbocyclization–borylation of enallenes that is catalyzed by palladium(II) and a Brønsted acid was developed. Biphenol‐type chiral phosphoric acids were superior co‐catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.
Biphenol‐artige chirale Phosphorsäuren induzieren als Cokatalysatoren Enantioselektivität in der Palladium(II)‐katalysierten oxidativen Carbocyclisierung‐Borylierung von Enallenen. Eine Anzahl enantiomerenangereicherter borylierter Carbocyclen wurde mit dieser Methode in hohen Ausbeuten und Enantioselektivitäten hergestellt. BQ=Benzochinon, pin=Pinakolato. |
| doi_str_mv | 10.1002/ange.201501048 |
| format | Article |
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Biphenol‐artige chirale Phosphorsäuren induzieren als Cokatalysatoren Enantioselektivität in der Palladium(II)‐katalysierten oxidativen Carbocyclisierung‐Borylierung von Enallenen. Eine Anzahl enantiomerenangereicherter borylierter Carbocyclen wurde mit dieser Methode in hohen Ausbeuten und Enantioselektivitäten hergestellt. BQ=Benzochinon, pin=Pinakolato.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201501048</identifier><language>eng ; ger</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Carbocyclisierung ; Chemistry ; Chirale Anionen ; Chirale Phosphorsäuren ; Oxidation ; Palladium</subject><ispartof>Angewandte Chemie, 2015-05, Vol.127 (20), p.6122-6125</ispartof><rights>2015 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non‐Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.</rights><rights>2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2408-b358e98dc513a42560de48beb57246b7a0c68ef5213126bfb3bf35235e7e43133</citedby><cites>FETCH-LOGICAL-c2408-b358e98dc513a42560de48beb57246b7a0c68ef5213126bfb3bf35235e7e43133</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.201501048$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201501048$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Jiang, Tuo</creatorcontrib><creatorcontrib>Bartholomeyzik, Teresa</creatorcontrib><creatorcontrib>Mazuela, Javier</creatorcontrib><creatorcontrib>Willersinn, Jochen</creatorcontrib><creatorcontrib>Bäckvall, Jan-E.</creatorcontrib><title>Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>An enantioselective oxidative carbocyclization–borylation of enallenes that is catalyzed by palladium(II) and a Brønsted acid was developed. Biphenol‐type chiral phosphoric acids were superior co‐catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.
Biphenol‐artige chirale Phosphorsäuren induzieren als Cokatalysatoren Enantioselektivität in der Palladium(II)‐katalysierten oxidativen Carbocyclisierung‐Borylierung von Enallenen. Eine Anzahl enantiomerenangereicherter borylierter Carbocyclen wurde mit dieser Methode in hohen Ausbeuten und Enantioselektivitäten hergestellt. BQ=Benzochinon, pin=Pinakolato.</description><subject>Carbocyclisierung</subject><subject>Chemistry</subject><subject>Chirale Anionen</subject><subject>Chirale Phosphorsäuren</subject><subject>Oxidation</subject><subject>Palladium</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkU1PwkAQhjdGExG9eibxoofifnbLEQGRhIjxIx4323ZqFpdWd4tSf5l3_5gLGOPN03zkfSYz7yB0THCXYEzPdfkEXYqJwATzZAe1iKAkYlLIXdTCmPMooby3jw68n2OMYyp7LTS_0dbq3CwXp5PJ2fmF-_osfQ15p5-ZPBroWtvmI5SjUpe1qTxYyGrzBp3ZyuR6kw20S6usyaz5CI2qjC4q19hN2qmKNWktlOAP0V6hrYejn9hGD5ej-8FVNJ2NJ4P-NMoox0mUMpFAL8kzQZjmVMQ4B56kkApJeZxKjbM4gSLcxgiN0yJlacEEZQIkcEYYa6OT7dwXV70uwddqXi1d2MIrEsskjMFUBlV3q8pc5b2DQr04s9CuUQSrtZ9q7af69TMAvS3wbiw0_6hV_3o8-stGW9YEb1e_rHbPKpbhQ-rxeqzYHb8dsiFVt-wb_-aJ5A</recordid><startdate>20150511</startdate><enddate>20150511</enddate><creator>Jiang, Tuo</creator><creator>Bartholomeyzik, Teresa</creator><creator>Mazuela, Javier</creator><creator>Willersinn, Jochen</creator><creator>Bäckvall, Jan-E.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>24P</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>20150511</creationdate><title>Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes</title><author>Jiang, Tuo ; Bartholomeyzik, Teresa ; Mazuela, Javier ; Willersinn, Jochen ; Bäckvall, Jan-E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2408-b358e98dc513a42560de48beb57246b7a0c68ef5213126bfb3bf35235e7e43133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; ger</language><creationdate>2015</creationdate><topic>Carbocyclisierung</topic><topic>Chemistry</topic><topic>Chirale Anionen</topic><topic>Chirale Phosphorsäuren</topic><topic>Oxidation</topic><topic>Palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Tuo</creatorcontrib><creatorcontrib>Bartholomeyzik, Teresa</creatorcontrib><creatorcontrib>Mazuela, Javier</creatorcontrib><creatorcontrib>Willersinn, Jochen</creatorcontrib><creatorcontrib>Bäckvall, Jan-E.</creatorcontrib><collection>Istex</collection><collection>Wiley-Blackwell Open Access Titles</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>Jiang, Tuo</au><au>Bartholomeyzik, Teresa</au><au>Mazuela, Javier</au><au>Willersinn, Jochen</au><au>Bäckvall, Jan-E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2015-05-11</date><risdate>2015</risdate><volume>127</volume><issue>20</issue><spage>6122</spage><epage>6125</epage><pages>6122-6125</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>An enantioselective oxidative carbocyclization–borylation of enallenes that is catalyzed by palladium(II) and a Brønsted acid was developed. Biphenol‐type chiral phosphoric acids were superior co‐catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.
Biphenol‐artige chirale Phosphorsäuren induzieren als Cokatalysatoren Enantioselektivität in der Palladium(II)‐katalysierten oxidativen Carbocyclisierung‐Borylierung von Enallenen. Eine Anzahl enantiomerenangereicherter borylierter Carbocyclen wurde mit dieser Methode in hohen Ausbeuten und Enantioselektivitäten hergestellt. BQ=Benzochinon, pin=Pinakolato.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201501048</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Carbocyclisierung Chemistry Chirale Anionen Chirale Phosphorsäuren Oxidation Palladium |
| title | Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes |
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