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Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions
The first highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization reaction. The spiro‐2H‐pyrrole derivatives readily undergo a controllable and stereospecific allylic migration under acid catalysis, pro...
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| Published in: | Angewandte Chemie International Edition 2015-07, Vol.54 (29), p.8475-8479 |
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| Main Authors: | , , , , |
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| cited_by | cdi_FETCH-LOGICAL-c6179-8bb13a71ba0d5499c551ce558cb849aae244e309c784e1ac984a315687c01cc43 |
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| cites | cdi_FETCH-LOGICAL-c6179-8bb13a71ba0d5499c551ce558cb849aae244e309c784e1ac984a315687c01cc43 |
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| container_issue | 29 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Zhuo, Chun-Xiang Cheng, Qiang Liu, Wen-Bo Zhao, Qiang You, Shu-Li |
| description | The first highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization reaction. The spiro‐2H‐pyrrole derivatives readily undergo a controllable and stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values. Additionally, the novel Ir‐complex K1, derived from [Ir(cod)Cl]2 (cod=1,5‐cyclooctadiene) and N‐benzhydryl‐N‐phenyldinaphthophosphoramidite (BHPphos), showed excellent control of both diastereo‐ and enantioselectivities.
It's all under control: The highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization. The spiro‐2H‐pyrrole derivatives readily undergo a stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values. |
| doi_str_mv | 10.1002/anie.201502259 |
| format | article |
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It's all under control: The highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization. The spiro‐2H‐pyrrole derivatives readily undergo a stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201502259</identifier><identifier>PMID: 26036866</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkadienes - chemistry ; Allyl Compounds - chemistry ; asymmetric catalysis ; Asymmetry ; Catalysis ; dearomatization ; Derivatives ; enantioselectivity ; iridium ; Iridium - chemistry ; Migration ; Pyrroles ; Pyrroles - chemistry ; Spiro Compounds - chemistry ; Stability ; Stereoisomerism ; stereospecific migration ; Synthesis</subject><ispartof>Angewandte Chemie International Edition, 2015-07, Vol.54 (29), p.8475-8479</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6179-8bb13a71ba0d5499c551ce558cb849aae244e309c784e1ac984a315687c01cc43</citedby><cites>FETCH-LOGICAL-c6179-8bb13a71ba0d5499c551ce558cb849aae244e309c784e1ac984a315687c01cc43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26036866$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhuo, Chun-Xiang</creatorcontrib><creatorcontrib>Cheng, Qiang</creatorcontrib><creatorcontrib>Liu, Wen-Bo</creatorcontrib><creatorcontrib>Zhao, Qiang</creatorcontrib><creatorcontrib>You, Shu-Li</creatorcontrib><title>Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>The first highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization reaction. The spiro‐2H‐pyrrole derivatives readily undergo a controllable and stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values. Additionally, the novel Ir‐complex K1, derived from [Ir(cod)Cl]2 (cod=1,5‐cyclooctadiene) and N‐benzhydryl‐N‐phenyldinaphthophosphoramidite (BHPphos), showed excellent control of both diastereo‐ and enantioselectivities.
It's all under control: The highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization. The spiro‐2H‐pyrrole derivatives readily undergo a stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values.</description><subject>Alkadienes - chemistry</subject><subject>Allyl Compounds - chemistry</subject><subject>asymmetric catalysis</subject><subject>Asymmetry</subject><subject>Catalysis</subject><subject>dearomatization</subject><subject>Derivatives</subject><subject>enantioselectivity</subject><subject>iridium</subject><subject>Iridium - chemistry</subject><subject>Migration</subject><subject>Pyrroles</subject><subject>Pyrroles - chemistry</subject><subject>Spiro Compounds - chemistry</subject><subject>Stability</subject><subject>Stereoisomerism</subject><subject>stereospecific migration</subject><subject>Synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkU9v0zAYhyMEYmNw5YgiceGSYsd_cyxZGYUxJgriaDnuW_Bw4mKn27KPxKfEWUaFuOxg2ZKf5_fa-mXZc4xmGKHyte4szEqEGSpLVj3IDjErcUGEIA_TmRJSCMnwQfYkxovES4n44-yg5Ihwyflh9nvR6a63PoID09tLyFdD1_-AaGPuN_n5EIJ3ULzREdb5amuDL3LdrfNz7wYzGGdNfgzBXurRjXkz5Mtg13bXFrXutRtukjaPQ9tCHxI7d26YHB18m6SbtHx3G1n7rk_DnG4c5B_t9zBdfQZtxkN8mj3aaBfh2d1-lH19u_hSvytOP50s6_lpYTgWVSGbBhMtcKPRmtGqMoxhA4xJ00haaQ0lpUBQZYSkgLWpJNUEMy6FQdgYSo6yV1PuNvhfO4i9am00kB7Wgd9FhQWlXJIS4_tRXnEpBUI8oS__Qy_8LnTpI7cUQpLycfZsokzwMQbYqG2wrQ6DwkiNhauxcLUvPAkv7mJ3TQvrPf634QRUE3BlHQz3xKn52XLxb3gxuTb2cL13dfipuCCCqW9nJwq9p2gl6w8Kkz9_9ckK</recordid><startdate>20150713</startdate><enddate>20150713</enddate><creator>Zhuo, Chun-Xiang</creator><creator>Cheng, Qiang</creator><creator>Liu, Wen-Bo</creator><creator>Zhao, Qiang</creator><creator>You, Shu-Li</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150713</creationdate><title>Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions</title><author>Zhuo, Chun-Xiang ; Cheng, Qiang ; Liu, Wen-Bo ; Zhao, Qiang ; You, Shu-Li</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6179-8bb13a71ba0d5499c551ce558cb849aae244e309c784e1ac984a315687c01cc43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkadienes - chemistry</topic><topic>Allyl Compounds - chemistry</topic><topic>asymmetric catalysis</topic><topic>Asymmetry</topic><topic>Catalysis</topic><topic>dearomatization</topic><topic>Derivatives</topic><topic>enantioselectivity</topic><topic>iridium</topic><topic>Iridium - chemistry</topic><topic>Migration</topic><topic>Pyrroles</topic><topic>Pyrroles - chemistry</topic><topic>Spiro Compounds - chemistry</topic><topic>Stability</topic><topic>Stereoisomerism</topic><topic>stereospecific migration</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhuo, Chun-Xiang</creatorcontrib><creatorcontrib>Cheng, Qiang</creatorcontrib><creatorcontrib>Liu, Wen-Bo</creatorcontrib><creatorcontrib>Zhao, Qiang</creatorcontrib><creatorcontrib>You, Shu-Li</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhuo, Chun-Xiang</au><au>Cheng, Qiang</au><au>Liu, Wen-Bo</au><au>Zhao, Qiang</au><au>You, Shu-Li</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-07-13</date><risdate>2015</risdate><volume>54</volume><issue>29</issue><spage>8475</spage><epage>8479</epage><pages>8475-8479</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>The first highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization reaction. The spiro‐2H‐pyrrole derivatives readily undergo a controllable and stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values. Additionally, the novel Ir‐complex K1, derived from [Ir(cod)Cl]2 (cod=1,5‐cyclooctadiene) and N‐benzhydryl‐N‐phenyldinaphthophosphoramidite (BHPphos), showed excellent control of both diastereo‐ and enantioselectivities.
It's all under control: The highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization. The spiro‐2H‐pyrrole derivatives readily undergo a stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26036866</pmid><doi>10.1002/anie.201502259</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Alkadienes - chemistry Allyl Compounds - chemistry asymmetric catalysis Asymmetry Catalysis dearomatization Derivatives enantioselectivity iridium Iridium - chemistry Migration Pyrroles Pyrroles - chemistry Spiro Compounds - chemistry Stability Stereoisomerism stereospecific migration Synthesis |
| title | Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions |
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