Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes

Constructing eight-membered rings, especially in an enantioselective manner, is a challenging task due to unfavorable enthalpic and entropic barriers of the transition states during the formation process. Here we report an asymmetric [4+4] annulation reaction of diverse 1-azadienes and β-substituted...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2020-07, Vol.56 (53), p.7257-726
Hauptverfasser:	Jiang, Bo, Du, Wei, Chen, Ying-Chun
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids Chemical reactions Crystallography Enantiomers Indene NMR Nuclear magnetic resonance
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	726
container_issue	53
container_start_page	7257
container_title	Chemical communications (Cambridge, England)
container_volume	56
creator	Jiang, Bo Du, Wei Chen, Ying-Chun
description	Constructing eight-membered rings, especially in an enantioselective manner, is a challenging task due to unfavorable enthalpic and entropic barriers of the transition states during the formation process. Here we report an asymmetric [4+4] annulation reaction of diverse 1-azadienes and β-substituted cyclobutenones under the catalysis of modified cinchona alkaloids, by the in situ generation of ring-opened ammonium dienolate intermediates. A spectrum of heteroarene- or indene-fused eight-membered lactams are obtained in fair to excellent yields with remarkable enantioselectivities (up to 99% yield, 99% ee). An asymmetric [4+4] annulation reaction between β-substituted cyclobutenones and diverse 1-azadienes is developed under the catalysis of modified cinchona alkaloids.
doi_str_mv	10.1039/d0cc02836c
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2419347313</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2419347313</sourcerecordid><originalsourceid>FETCH-LOGICAL-c363t-8ed2adad2d8c4c9aa3ff7ea2809c6f17fde89285de0c0a692973c3691f18b3f73</originalsourceid><addsrcrecordid>eNp9kc9rFTEQx0NR7A-9eFdWeinKarLJ7iZH2bYqVLxYKBRZ5k0mmJqXPDe7wvOvN_XVCh7MJRk-nwzDfBl7KvhrwaV5Yzkib7TscI8dCNmpulX66sHtuzV1L1W7zw5zvuHliFY_YvuyUZ3hQhww_zFZ7zzZCn3ErylCBeEbhORtjTBD2ObCKEKcfcoUCGf_g6pr9Up9qSDGJUABMVfJVbjFkFbLTDFFyoXaStTwE6ynUj9mDx2ETE_u7iN2eX72eXhfX3x692F4e1Gj7ORca7INWLCN1ajQAEjneoJGc4OdE72zpE2jW0scOXSmMb0sP41wQq-k6-URO9n13Uzp-0J5Htc-I4UAkdKSx0ZxLYw2pivq8T_qTVqmWKYrljBS9VLIYr3cWTilnCdy42bya5i2o-DjbQDjKR-G3wEMRX5-13JZrcneq382XoRnO2HKeE__Jlj4i__xcWOd_AWF3Zam</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2419347313</pqid></control><display><type>article</type><title>Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Jiang, Bo ; Du, Wei ; Chen, Ying-Chun</creator><creatorcontrib>Jiang, Bo ; Du, Wei ; Chen, Ying-Chun</creatorcontrib><description>Constructing eight-membered rings, especially in an enantioselective manner, is a challenging task due to unfavorable enthalpic and entropic barriers of the transition states during the formation process. Here we report an asymmetric [4+4] annulation reaction of diverse 1-azadienes and β-substituted cyclobutenones under the catalysis of modified cinchona alkaloids, by the in situ generation of ring-opened ammonium dienolate intermediates. A spectrum of heteroarene- or indene-fused eight-membered lactams are obtained in fair to excellent yields with remarkable enantioselectivities (up to 99% yield, 99% ee). An asymmetric [4+4] annulation reaction between β-substituted cyclobutenones and diverse 1-azadienes is developed under the catalysis of modified cinchona alkaloids.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d0cc02836c</identifier><identifier>PMID: 32469011</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkaloids ; Chemical reactions ; Crystallography ; Enantiomers ; Indene ; NMR ; Nuclear magnetic resonance</subject><ispartof>Chemical communications (Cambridge, England), 2020-07, Vol.56 (53), p.7257-726</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-8ed2adad2d8c4c9aa3ff7ea2809c6f17fde89285de0c0a692973c3691f18b3f73</citedby><cites>FETCH-LOGICAL-c363t-8ed2adad2d8c4c9aa3ff7ea2809c6f17fde89285de0c0a692973c3691f18b3f73</cites><orcidid>0000-0003-1902-0979 ; 0000-0003-4162-1471</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32469011$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jiang, Bo</creatorcontrib><creatorcontrib>Du, Wei</creatorcontrib><creatorcontrib>Chen, Ying-Chun</creatorcontrib><title>Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Constructing eight-membered rings, especially in an enantioselective manner, is a challenging task due to unfavorable enthalpic and entropic barriers of the transition states during the formation process. Here we report an asymmetric [4+4] annulation reaction of diverse 1-azadienes and β-substituted cyclobutenones under the catalysis of modified cinchona alkaloids, by the in situ generation of ring-opened ammonium dienolate intermediates. A spectrum of heteroarene- or indene-fused eight-membered lactams are obtained in fair to excellent yields with remarkable enantioselectivities (up to 99% yield, 99% ee). An asymmetric [4+4] annulation reaction between β-substituted cyclobutenones and diverse 1-azadienes is developed under the catalysis of modified cinchona alkaloids.</description><subject>Alkaloids</subject><subject>Chemical reactions</subject><subject>Crystallography</subject><subject>Enantiomers</subject><subject>Indene</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kc9rFTEQx0NR7A-9eFdWeinKarLJ7iZH2bYqVLxYKBRZ5k0mmJqXPDe7wvOvN_XVCh7MJRk-nwzDfBl7KvhrwaV5Yzkib7TscI8dCNmpulX66sHtuzV1L1W7zw5zvuHliFY_YvuyUZ3hQhww_zFZ7zzZCn3ErylCBeEbhORtjTBD2ObCKEKcfcoUCGf_g6pr9Up9qSDGJUABMVfJVbjFkFbLTDFFyoXaStTwE6ynUj9mDx2ETE_u7iN2eX72eXhfX3x692F4e1Gj7ORca7INWLCN1ajQAEjneoJGc4OdE72zpE2jW0scOXSmMb0sP41wQq-k6-URO9n13Uzp-0J5Htc-I4UAkdKSx0ZxLYw2pivq8T_qTVqmWKYrljBS9VLIYr3cWTilnCdy42bya5i2o-DjbQDjKR-G3wEMRX5-13JZrcneq382XoRnO2HKeE__Jlj4i__xcWOd_AWF3Zam</recordid><startdate>20200707</startdate><enddate>20200707</enddate><creator>Jiang, Bo</creator><creator>Du, Wei</creator><creator>Chen, Ying-Chun</creator><general>Royal Society of Chemistry</general><scope>NPM</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><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1902-0979</orcidid><orcidid>https://orcid.org/0000-0003-4162-1471</orcidid></search><sort><creationdate>20200707</creationdate><title>Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes</title><author>Jiang, Bo ; Du, Wei ; Chen, Ying-Chun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-8ed2adad2d8c4c9aa3ff7ea2809c6f17fde89285de0c0a692973c3691f18b3f73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkaloids</topic><topic>Chemical reactions</topic><topic>Crystallography</topic><topic>Enantiomers</topic><topic>Indene</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Bo</creatorcontrib><creatorcontrib>Du, Wei</creatorcontrib><creatorcontrib>Chen, Ying-Chun</creatorcontrib><collection>PubMed</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><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Bo</au><au>Du, Wei</au><au>Chen, Ying-Chun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-07-07</date><risdate>2020</risdate><volume>56</volume><issue>53</issue><spage>7257</spage><epage>726</epage><pages>7257-726</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Constructing eight-membered rings, especially in an enantioselective manner, is a challenging task due to unfavorable enthalpic and entropic barriers of the transition states during the formation process. Here we report an asymmetric [4+4] annulation reaction of diverse 1-azadienes and β-substituted cyclobutenones under the catalysis of modified cinchona alkaloids, by the in situ generation of ring-opened ammonium dienolate intermediates. A spectrum of heteroarene- or indene-fused eight-membered lactams are obtained in fair to excellent yields with remarkable enantioselectivities (up to 99% yield, 99% ee). An asymmetric [4+4] annulation reaction between β-substituted cyclobutenones and diverse 1-azadienes is developed under the catalysis of modified cinchona alkaloids.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32469011</pmid><doi>10.1039/d0cc02836c</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-1902-0979</orcidid><orcidid>https://orcid.org/0000-0003-4162-1471</orcidid></addata></record>
fulltext	fulltext
identifier	ISSN: 1359-7345
ispartof	Chemical communications (Cambridge, England), 2020-07, Vol.56 (53), p.7257-726
issn	1359-7345 1364-548X
language	eng
recordid	cdi_proquest_journals_2419347313
source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Alkaloids Chemical reactions Crystallography Enantiomers Indene NMR Nuclear magnetic resonance
title	Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-20T06%3A56%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Modified%20cinchona%20alkaloid-catalysed%20enantioselective%20%5B4+4%5D%20annulations%20of%20cyclobutenones%20and%201-azadienes&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Jiang,%20Bo&rft.date=2020-07-07&rft.volume=56&rft.issue=53&rft.spage=7257&rft.epage=726&rft.pages=7257-726&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d0cc02836c&rft_dat=%3Cproquest_cross%3E2419347313%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2419347313&rft_id=info:pmid/32469011&rfr_iscdi=true