Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid
The first enantioselective polyene cyclization initiated by a BINOL‐derived chiral N‐phosphoramide (NPA) catalyzed protonation of an imine is described. The ion‐pair formed between the iminium ion and chiral counter anion of the NPA plays an important role for controlling the stereochemistry of the...
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| Veröffentlicht in: | Angewandte Chemie 2018-02, Vol.130 (8), p.2137-2141 |
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| container_title | Angewandte Chemie |
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| creator | Fan, Liwen Han, Chunyu Li, Xuerong Yao, Jiasheng Wang, Zhengning Yao, Chaochao Chen, Weihao Wang, Tao Zhao, Junfeng |
| description | The first enantioselective polyene cyclization initiated by a BINOL‐derived chiral N‐phosphoramide (NPA) catalyzed protonation of an imine is described. The ion‐pair formed between the iminium ion and chiral counter anion of the NPA plays an important role for controlling the stereochemistry of the overall transformation. This strategy offers a highly efficient approach to fused tricyclic frameworks containing three contiguous stereocenters, which are widely found in natural products. In addition, the first catalytic asymmetric total synthesis of (−)‐ferruginol was accomplished with an NPA catalyzed enantioselective polyene cyclization, as the key step for the construction of the tricyclic core, with excellent yield and enantioselectivity.
Ein zielstrebiges Paar: Die erste enantioselektive Polyencyclisierung, die durch eine BINOL‐N‐Phosphoramid(NPA)‐katalysierte Protonierung eines Imins ausgelöst wird, wird beschrieben. Das Ionenpaar, das zwischen dem Iminiumion und chiralen Gegenion des NPA gebildet wird, spielt eine wichtige Rolle für die Stereochemie der Gesamtumwandlung. Die Methode wurde zur ersten katalytischen Totalsynthese von (−)‐Ferruginol verwendet. |
| doi_str_mv | 10.1002/ange.201711603 |
| format | Article |
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Ein zielstrebiges Paar: Die erste enantioselektive Polyencyclisierung, die durch eine BINOL‐N‐Phosphoramid(NPA)‐katalysierte Protonierung eines Imins ausgelöst wird, wird beschrieben. Das Ionenpaar, das zwischen dem Iminiumion und chiralen Gegenion des NPA gebildet wird, spielt eine wichtige Rolle für die Stereochemie der Gesamtumwandlung. Die Methode wurde zur ersten katalytischen Totalsynthese von (−)‐Ferruginol verwendet.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201711603</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Asymmetrische Synthesen ; Catalysis ; Chemical synthesis ; Chemistry ; Chirale Brønsted-Säuren ; Enantiomers ; Natural products ; Polyencyclisierungen ; Protonation ; Stereochemistry ; Terpene ; Totalsynthesen</subject><ispartof>Angewandte Chemie, 2018-02, Vol.130 (8), p.2137-2141</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1623-13bf25babf67c0ed5c3baa5c45ec342dd4120c719f6c5ac2fe46449fe3f7af603</citedby><cites>FETCH-LOGICAL-c1623-13bf25babf67c0ed5c3baa5c45ec342dd4120c719f6c5ac2fe46449fe3f7af603</cites><orcidid>0000-0003-4843-4871</orcidid></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.201711603$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201711603$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Fan, Liwen</creatorcontrib><creatorcontrib>Han, Chunyu</creatorcontrib><creatorcontrib>Li, Xuerong</creatorcontrib><creatorcontrib>Yao, Jiasheng</creatorcontrib><creatorcontrib>Wang, Zhengning</creatorcontrib><creatorcontrib>Yao, Chaochao</creatorcontrib><creatorcontrib>Chen, Weihao</creatorcontrib><creatorcontrib>Wang, Tao</creatorcontrib><creatorcontrib>Zhao, Junfeng</creatorcontrib><title>Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid</title><title>Angewandte Chemie</title><description>The first enantioselective polyene cyclization initiated by a BINOL‐derived chiral N‐phosphoramide (NPA) catalyzed protonation of an imine is described. The ion‐pair formed between the iminium ion and chiral counter anion of the NPA plays an important role for controlling the stereochemistry of the overall transformation. This strategy offers a highly efficient approach to fused tricyclic frameworks containing three contiguous stereocenters, which are widely found in natural products. In addition, the first catalytic asymmetric total synthesis of (−)‐ferruginol was accomplished with an NPA catalyzed enantioselective polyene cyclization, as the key step for the construction of the tricyclic core, with excellent yield and enantioselectivity.
Ein zielstrebiges Paar: Die erste enantioselektive Polyencyclisierung, die durch eine BINOL‐N‐Phosphoramid(NPA)‐katalysierte Protonierung eines Imins ausgelöst wird, wird beschrieben. Das Ionenpaar, das zwischen dem Iminiumion und chiralen Gegenion des NPA gebildet wird, spielt eine wichtige Rolle für die Stereochemie der Gesamtumwandlung. Die Methode wurde zur ersten katalytischen Totalsynthese von (−)‐Ferruginol verwendet.</description><subject>Asymmetrische Synthesen</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chirale Brønsted-Säuren</subject><subject>Enantiomers</subject><subject>Natural products</subject><subject>Polyencyclisierungen</subject><subject>Protonation</subject><subject>Stereochemistry</subject><subject>Terpene</subject><subject>Totalsynthesen</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EEqWwMkdiTjl_xWQsUSmVKmCA2XKcM7gKSbFTUPrL2PljpCqCkemku_e50z2EnFOYUAB2aZpnnDCgitIM-AEZUcloypVUh2QEIER6xUR-TE5iXAFAxlQ-IotZY5rOtxFrtJ1_x-ShrXtsMCl6W_utGWZNUpjO1P0Wq6TsE5MULz6YOrkOX59N7Ibu1PrqlBw5U0c8-6lj8nQzeyxu0-X9fFFMl6mlGeMp5aVjsjSly5QFrKTlpTHSComWC1ZVgjKwiuYus9JY5lBkQuQOuVPGDY-NycV-7zq0bxuMnV61m9AMJzUDoJyzjKohNdmnbGhjDOj0OvhXE3pNQe906Z0u_atrAPI98OFr7P9J6-ndfPbHfgMPFW-Y</recordid><startdate>20180219</startdate><enddate>20180219</enddate><creator>Fan, Liwen</creator><creator>Han, Chunyu</creator><creator>Li, Xuerong</creator><creator>Yao, Jiasheng</creator><creator>Wang, Zhengning</creator><creator>Yao, Chaochao</creator><creator>Chen, Weihao</creator><creator>Wang, Tao</creator><creator>Zhao, Junfeng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-4843-4871</orcidid></search><sort><creationdate>20180219</creationdate><title>Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid</title><author>Fan, Liwen ; Han, Chunyu ; Li, Xuerong ; Yao, Jiasheng ; Wang, Zhengning ; Yao, Chaochao ; Chen, Weihao ; Wang, Tao ; Zhao, Junfeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1623-13bf25babf67c0ed5c3baa5c45ec342dd4120c719f6c5ac2fe46449fe3f7af603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Asymmetrische Synthesen</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chirale Brønsted-Säuren</topic><topic>Enantiomers</topic><topic>Natural products</topic><topic>Polyencyclisierungen</topic><topic>Protonation</topic><topic>Stereochemistry</topic><topic>Terpene</topic><topic>Totalsynthesen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fan, Liwen</creatorcontrib><creatorcontrib>Han, Chunyu</creatorcontrib><creatorcontrib>Li, Xuerong</creatorcontrib><creatorcontrib>Yao, Jiasheng</creatorcontrib><creatorcontrib>Wang, Zhengning</creatorcontrib><creatorcontrib>Yao, Chaochao</creatorcontrib><creatorcontrib>Chen, Weihao</creatorcontrib><creatorcontrib>Wang, Tao</creatorcontrib><creatorcontrib>Zhao, Junfeng</creatorcontrib><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>Fan, Liwen</au><au>Han, Chunyu</au><au>Li, Xuerong</au><au>Yao, Jiasheng</au><au>Wang, Zhengning</au><au>Yao, Chaochao</au><au>Chen, Weihao</au><au>Wang, Tao</au><au>Zhao, Junfeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid</atitle><jtitle>Angewandte Chemie</jtitle><date>2018-02-19</date><risdate>2018</risdate><volume>130</volume><issue>8</issue><spage>2137</spage><epage>2141</epage><pages>2137-2141</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The first enantioselective polyene cyclization initiated by a BINOL‐derived chiral N‐phosphoramide (NPA) catalyzed protonation of an imine is described. The ion‐pair formed between the iminium ion and chiral counter anion of the NPA plays an important role for controlling the stereochemistry of the overall transformation. This strategy offers a highly efficient approach to fused tricyclic frameworks containing three contiguous stereocenters, which are widely found in natural products. In addition, the first catalytic asymmetric total synthesis of (−)‐ferruginol was accomplished with an NPA catalyzed enantioselective polyene cyclization, as the key step for the construction of the tricyclic core, with excellent yield and enantioselectivity.
Ein zielstrebiges Paar: Die erste enantioselektive Polyencyclisierung, die durch eine BINOL‐N‐Phosphoramid(NPA)‐katalysierte Protonierung eines Imins ausgelöst wird, wird beschrieben. Das Ionenpaar, das zwischen dem Iminiumion und chiralen Gegenion des NPA gebildet wird, spielt eine wichtige Rolle für die Stereochemie der Gesamtumwandlung. Die Methode wurde zur ersten katalytischen Totalsynthese von (−)‐Ferruginol verwendet.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201711603</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-4843-4871</orcidid></addata></record> |
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| subjects | Asymmetrische Synthesen Catalysis Chemical synthesis Chemistry Chirale Brønsted-Säuren Enantiomers Natural products Polyencyclisierungen Protonation Stereochemistry Terpene Totalsynthesen |
| title | Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid |
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