Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines
Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade pro...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-10, Vol.59 (42), p.18452-18456 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Tian, Jun‐Jie Yang, Zhao‐Ying Liang, Xin‐Shen Liu, Ning Hu, Chen‐Yu Tu, Xian‐Shuang Li, Xiang Wang, Xiao‐Chen |
| description | Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.
A protocol for Lewis acid‐catalyzed highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been developed. The reactions were catalyzed by chiral spiro‐bicyclic bisboranes and occurred under mild reaction conditions with high turnover numbers. |
| doi_str_mv | 10.1002/anie.202007352 |
| format | Article |
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A protocol for Lewis acid‐catalyzed highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been developed. The reactions were catalyzed by chiral spiro‐bicyclic bisboranes and occurred under mild reaction conditions with high turnover numbers.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202007352</identifier><identifier>PMID: 32640060</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>asymmetric catalysis ; boron ; Catalysts ; Chemical reduction ; Dihydropyridine ; Enantiomers ; heterocycles ; Heterocyclic compounds ; Hydroboration ; Natural products ; pyridine ; Pyridines ; Reagents ; reduction ; Substitutes</subject><ispartof>Angewandte Chemie International Edition, 2020-10, Vol.59 (42), p.18452-18456</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2020 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4102-b8b5628865cd1fbea34494a38b465f9c47df0a4290cecc9df5237f084acaa2373</citedby><cites>FETCH-LOGICAL-c4102-b8b5628865cd1fbea34494a38b465f9c47df0a4290cecc9df5237f084acaa2373</cites><orcidid>0000-0001-5863-0804</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%2Fanie.202007352$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202007352$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32640060$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tian, Jun‐Jie</creatorcontrib><creatorcontrib>Yang, Zhao‐Ying</creatorcontrib><creatorcontrib>Liang, Xin‐Shen</creatorcontrib><creatorcontrib>Liu, Ning</creatorcontrib><creatorcontrib>Hu, Chen‐Yu</creatorcontrib><creatorcontrib>Tu, Xian‐Shuang</creatorcontrib><creatorcontrib>Li, Xiang</creatorcontrib><creatorcontrib>Wang, Xiao‐Chen</creatorcontrib><title>Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.
A protocol for Lewis acid‐catalyzed highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been developed. The reactions were catalyzed by chiral spiro‐bicyclic bisboranes and occurred under mild reaction conditions with high turnover numbers.</description><subject>asymmetric catalysis</subject><subject>boron</subject><subject>Catalysts</subject><subject>Chemical reduction</subject><subject>Dihydropyridine</subject><subject>Enantiomers</subject><subject>heterocycles</subject><subject>Heterocyclic compounds</subject><subject>Hydroboration</subject><subject>Natural products</subject><subject>pyridine</subject><subject>Pyridines</subject><subject>Reagents</subject><subject>reduction</subject><subject>Substitutes</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkT1PwzAQhi0EoqWwMqJILCwpju04yViiApUqQHytkWNfhKvUKXECChM_gd_IL8Gl5UMsTHeynnt0vheh_QAPA4zJsTAahgQTjCMakg3UD0IS-DSK6KbrGaV-FIdBD-1YO3N8HGO-jXqUcIYxx30EJ1UtDLy_vqWiEWX3AspLH2BeWShBNvoJPGGUNzbCNPrX4zWo1nWV8arCI278XpuudPWmzW2jm7Zxoquu1kobsLtoqxClhb11HaC70_Fteu5PL88m6WjqSxZg4udxHnK3Iw-lCoocBGUsYYLGOeNhkUgWqQILRhIsQcpEFSGhUYFjJqQQrqUDdLTyLurqsQXbZHNtJZSl-2LV2oww4i7FE04cevgHnVVtbdx2jmIx4Tz-FA5XlKwra2soskWt56LusgBnywCyZQDZdwBu4GCtbfM5qG_86-IOSFbAsy6h-0eXjS4m4x_5B85PlaE</recordid><startdate>20201012</startdate><enddate>20201012</enddate><creator>Tian, Jun‐Jie</creator><creator>Yang, Zhao‐Ying</creator><creator>Liang, Xin‐Shen</creator><creator>Liu, Ning</creator><creator>Hu, Chen‐Yu</creator><creator>Tu, Xian‐Shuang</creator><creator>Li, Xiang</creator><creator>Wang, Xiao‐Chen</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5863-0804</orcidid></search><sort><creationdate>20201012</creationdate><title>Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines</title><author>Tian, Jun‐Jie ; Yang, Zhao‐Ying ; Liang, Xin‐Shen ; Liu, Ning ; Hu, Chen‐Yu ; Tu, Xian‐Shuang ; Li, Xiang ; Wang, Xiao‐Chen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4102-b8b5628865cd1fbea34494a38b465f9c47df0a4290cecc9df5237f084acaa2373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>asymmetric catalysis</topic><topic>boron</topic><topic>Catalysts</topic><topic>Chemical reduction</topic><topic>Dihydropyridine</topic><topic>Enantiomers</topic><topic>heterocycles</topic><topic>Heterocyclic compounds</topic><topic>Hydroboration</topic><topic>Natural products</topic><topic>pyridine</topic><topic>Pyridines</topic><topic>Reagents</topic><topic>reduction</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tian, Jun‐Jie</creatorcontrib><creatorcontrib>Yang, Zhao‐Ying</creatorcontrib><creatorcontrib>Liang, Xin‐Shen</creatorcontrib><creatorcontrib>Liu, Ning</creatorcontrib><creatorcontrib>Hu, Chen‐Yu</creatorcontrib><creatorcontrib>Tu, Xian‐Shuang</creatorcontrib><creatorcontrib>Li, Xiang</creatorcontrib><creatorcontrib>Wang, Xiao‐Chen</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tian, Jun‐Jie</au><au>Yang, Zhao‐Ying</au><au>Liang, Xin‐Shen</au><au>Liu, Ning</au><au>Hu, Chen‐Yu</au><au>Tu, Xian‐Shuang</au><au>Li, Xiang</au><au>Wang, Xiao‐Chen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-10-12</date><risdate>2020</risdate><volume>59</volume><issue>42</issue><spage>18452</spage><epage>18456</epage><pages>18452-18456</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | asymmetric catalysis boron Catalysts Chemical reduction Dihydropyridine Enantiomers heterocycles Heterocyclic compounds Hydroboration Natural products pyridine Pyridines Reagents reduction Substitutes |
| title | Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines |
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