Phosphine‐Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers
Construction of contiguous all‐carbon quaternary stereogenic centers is a long‐standing challenge in synthetic organic chemistry. In this report, a phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos, containing either two identical or different oxindole moi...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2019-05, Vol.58 (19), p.6260-6264 |
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| creator | Chan, Wai‐Lun Tang, Xiaodong Zhang, Fuhao Quek, Glenn Mei, Guang‐Jian Lu, Yixin |
| description | Construction of contiguous all‐carbon quaternary stereogenic centers is a long‐standing challenge in synthetic organic chemistry. In this report, a phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos, containing either two identical or different oxindole moieties, is introduced as a powerful strategy for the construction of spirocyclic bisindoline alkaloid core structures. The reported reactions feature high chemical yields, excellent enantioselectivities, and very good regioselectivities, and are highly useful for creating structurally challenging bisindoline natural products.
Strategic move: The phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos is introduced as a powerful strategy for the construction of structural motifs containing two vicinal quaternary stereogenic centers. The reactions feature high yields, enantioselectivities, and regioselectivities, and are highly useful for creating structurally challenging hexahydropyrroloindoles (HPIs). |
| doi_str_mv | 10.1002/anie.201900758 |
| format | Article |
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Strategic move: The phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos is introduced as a powerful strategy for the construction of structural motifs containing two vicinal quaternary stereogenic centers. The reactions feature high yields, enantioselectivities, and regioselectivities, and are highly useful for creating structurally challenging hexahydropyrroloindoles (HPIs).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201900758</identifier><identifier>PMID: 30746821</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>alkaloids ; allenes ; annulations ; Chemical reactions ; Construction ; Enantiomers ; Natural products ; Organic chemistry ; organocatalysis ; Phosphine ; spiro compounds</subject><ispartof>Angewandte Chemie International Edition, 2019-05, Vol.58 (19), p.6260-6264</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4108-38420308b6be59a2756b3ab3a3fbfd16107663344fd63341baee173ff544717d3</citedby><cites>FETCH-LOGICAL-c4108-38420308b6be59a2756b3ab3a3fbfd16107663344fd63341baee173ff544717d3</cites><orcidid>0000-0002-5730-166X</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.201900758$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201900758$$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/30746821$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chan, Wai‐Lun</creatorcontrib><creatorcontrib>Tang, Xiaodong</creatorcontrib><creatorcontrib>Zhang, Fuhao</creatorcontrib><creatorcontrib>Quek, Glenn</creatorcontrib><creatorcontrib>Mei, Guang‐Jian</creatorcontrib><creatorcontrib>Lu, Yixin</creatorcontrib><title>Phosphine‐Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Construction of contiguous all‐carbon quaternary stereogenic centers is a long‐standing challenge in synthetic organic chemistry. In this report, a phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos, containing either two identical or different oxindole moieties, is introduced as a powerful strategy for the construction of spirocyclic bisindoline alkaloid core structures. The reported reactions feature high chemical yields, excellent enantioselectivities, and very good regioselectivities, and are highly useful for creating structurally challenging bisindoline natural products.
Strategic move: The phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos is introduced as a powerful strategy for the construction of structural motifs containing two vicinal quaternary stereogenic centers. The reactions feature high yields, enantioselectivities, and regioselectivities, and are highly useful for creating structurally challenging hexahydropyrroloindoles (HPIs).</description><subject>alkaloids</subject><subject>allenes</subject><subject>annulations</subject><subject>Chemical reactions</subject><subject>Construction</subject><subject>Enantiomers</subject><subject>Natural products</subject><subject>Organic chemistry</subject><subject>organocatalysis</subject><subject>Phosphine</subject><subject>spiro compounds</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkU9rGzEQxUVoSdK01xyLoJeUsu7oz67k3IxxWkNoUprmumh3Z2MFWXJWuzHuqfde-hn7SSrj1IVeCgPzBn7vwfAIOWUwYgD8vfEWRxzYGEDl-oAcs5yzTCglniUthciUztkReRHjfeK1huKQHAlQstCcHZMf14sQVwvr8df3n1PTG7f5hg09E-_4WzrxfnCmt8HT0NJ5DNY39i5Eurb9gk6cQ4_xnM688QmK6LDu7SPSi9At97abdaC3trbeOPp5MD123nQb-iUJDHfobU2n6NMVX5LnrXERXz3tE_L1YnYz_ZhdXn2YTyeXWS0Z6ExoyUGArooK87HhKi8qYdKItmobVjBQRSGElG2zXawyiEyJts2lVEw14oSc7XJXXXgYMPbl0sYanTMewxBLzrQCLkGxhL75B70PQ3rAJYozAbkGMU7UaEfVXYixw7ZcdXaZviwZlNuaym1N5b6mZHj9FDtUS2z2-J9eEjDeAWvrcPOfuHLyaT77G_4bWkCf5g</recordid><startdate>20190506</startdate><enddate>20190506</enddate><creator>Chan, Wai‐Lun</creator><creator>Tang, Xiaodong</creator><creator>Zhang, Fuhao</creator><creator>Quek, Glenn</creator><creator>Mei, Guang‐Jian</creator><creator>Lu, Yixin</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/0000-0002-5730-166X</orcidid></search><sort><creationdate>20190506</creationdate><title>Phosphine‐Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers</title><author>Chan, Wai‐Lun ; Tang, Xiaodong ; Zhang, Fuhao ; Quek, Glenn ; Mei, Guang‐Jian ; Lu, Yixin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4108-38420308b6be59a2756b3ab3a3fbfd16107663344fd63341baee173ff544717d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>alkaloids</topic><topic>allenes</topic><topic>annulations</topic><topic>Chemical reactions</topic><topic>Construction</topic><topic>Enantiomers</topic><topic>Natural products</topic><topic>Organic chemistry</topic><topic>organocatalysis</topic><topic>Phosphine</topic><topic>spiro compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chan, Wai‐Lun</creatorcontrib><creatorcontrib>Tang, Xiaodong</creatorcontrib><creatorcontrib>Zhang, Fuhao</creatorcontrib><creatorcontrib>Quek, Glenn</creatorcontrib><creatorcontrib>Mei, Guang‐Jian</creatorcontrib><creatorcontrib>Lu, Yixin</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>Chan, Wai‐Lun</au><au>Tang, Xiaodong</au><au>Zhang, Fuhao</au><au>Quek, Glenn</au><au>Mei, Guang‐Jian</au><au>Lu, Yixin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phosphine‐Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-05-06</date><risdate>2019</risdate><volume>58</volume><issue>19</issue><spage>6260</spage><epage>6264</epage><pages>6260-6264</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Construction of contiguous all‐carbon quaternary stereogenic centers is a long‐standing challenge in synthetic organic chemistry. In this report, a phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos, containing either two identical or different oxindole moieties, is introduced as a powerful strategy for the construction of spirocyclic bisindoline alkaloid core structures. The reported reactions feature high chemical yields, excellent enantioselectivities, and very good regioselectivities, and are highly useful for creating structurally challenging bisindoline natural products.
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | alkaloids allenes annulations Chemical reactions Construction Enantiomers Natural products Organic chemistry organocatalysis Phosphine spiro compounds |
| title | Phosphine‐Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers |
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