Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO t Bu-Mediated Cyclotrimerization of Aryl Vinyl Ketones

Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO t Bu-Mediated Cyclotrimerization of Aryl Vinyl Ketones

Herein, we disclose a simple one-pot method for an efficient regio- and stereoselective synthesis of 1,3,5-triaroylcyclohexanes from aryl vinyl ketones using potassium tert-butoxide. The developed protocol allows the construction of various symmetrically substituted cyclohexanes in good to excellent...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2024-12, Vol.89 (23), p.17207-17212
Hauptverfasser: Mahale, Sachin D., Yadav, Vinita, Gonnade, Rajesh G., Mhaske, Santosh B.
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 17212
container_issue 23
container_start_page 17207
container_title Journal of organic chemistry
container_volume 89
creator Mahale, Sachin D.
Yadav, Vinita
Gonnade, Rajesh G.
Mhaske, Santosh B.
description Herein, we disclose a simple one-pot method for an efficient regio- and stereoselective synthesis of 1,3,5-triaroylcyclohexanes from aryl vinyl ketones using potassium tert-butoxide. The developed protocol allows the construction of various symmetrically substituted cyclohexanes in good to excellent yields. The major product 2 also can be converted to the product 3 (all equatorial) conveniently by acid catalysis. This protocol features a good substrate scope and functional group compatibility.
doi_str_mv 10.1021/acs.joc.4c01695
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_joc_4c01695</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>b612562526</sourcerecordid><originalsourceid>FETCH-LOGICAL-a184t-5c9bc98819a9a671a78fbd663accecb435a00b9e65d1c727e8f027901aa4cbdd3</originalsourceid><addsrcrecordid>eNp1kM1PwzAMxSMEYmNw5oZyZ92Stmmb45j40kCTYHCt3NSFTl0zJe3EuPKPk6kbN3ywZem9J_tHyCVnI858PgZlR0utRqFiPJLiiPS58JkXSRYekz5jvu8FfhT0yJm1S-ZKCHFKeoEUgeBh0ic_L_hRao9CndPXBg1qixWqptwgneraNqZ1i66pLigfBkPhLUwJRm8rtVWV_sQvqNHSTQl0NqcNvWm9Z8xLaDCn052iMeUKTfkNh5SJ2Vb0vaxdn2GjnfucnBRQWbzYzwF5u7tdTB-8p_n943Ty5AFPwsYTSmZKJgmXICGKOcRJkeVRFIBSqLIwEMBYJjESOVexH2NSMD-WjAOEKsvzYEDGXa4y2lqDRbp2x4HZppylO5ypw5k6nOkep3NcdY51m60w_9Mf-DnBdSfonK2p3QP_xv0CGQyCtw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO t Bu-Mediated Cyclotrimerization of Aryl Vinyl Ketones</title><source>American Chemical Society Journals</source><creator>Mahale, Sachin D. ; Yadav, Vinita ; Gonnade, Rajesh G. ; Mhaske, Santosh B.</creator><creatorcontrib>Mahale, Sachin D. ; Yadav, Vinita ; Gonnade, Rajesh G. ; Mhaske, Santosh B.</creatorcontrib><description>Herein, we disclose a simple one-pot method for an efficient regio- and stereoselective synthesis of 1,3,5-triaroylcyclohexanes from aryl vinyl ketones using potassium tert-butoxide. The developed protocol allows the construction of various symmetrically substituted cyclohexanes in good to excellent yields. The major product 2 also can be converted to the product 3 (all equatorial) conveniently by acid catalysis. This protocol features a good substrate scope and functional group compatibility.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.4c01695</identifier><identifier>PMID: 39535148</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2024-12, Vol.89 (23), p.17207-17212</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a184t-5c9bc98819a9a671a78fbd663accecb435a00b9e65d1c727e8f027901aa4cbdd3</cites><orcidid>0000-0002-2841-0197 ; 0000-0002-5859-0838</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.4c01695$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.4c01695$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39535148$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mahale, Sachin D.</creatorcontrib><creatorcontrib>Yadav, Vinita</creatorcontrib><creatorcontrib>Gonnade, Rajesh G.</creatorcontrib><creatorcontrib>Mhaske, Santosh B.</creatorcontrib><title>Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO t Bu-Mediated Cyclotrimerization of Aryl Vinyl Ketones</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Herein, we disclose a simple one-pot method for an efficient regio- and stereoselective synthesis of 1,3,5-triaroylcyclohexanes from aryl vinyl ketones using potassium tert-butoxide. The developed protocol allows the construction of various symmetrically substituted cyclohexanes in good to excellent yields. The major product 2 also can be converted to the product 3 (all equatorial) conveniently by acid catalysis. This protocol features a good substrate scope and functional group compatibility.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kM1PwzAMxSMEYmNw5oZyZ92Stmmb45j40kCTYHCt3NSFTl0zJe3EuPKPk6kbN3ywZem9J_tHyCVnI858PgZlR0utRqFiPJLiiPS58JkXSRYekz5jvu8FfhT0yJm1S-ZKCHFKeoEUgeBh0ic_L_hRao9CndPXBg1qixWqptwgneraNqZ1i66pLigfBkPhLUwJRm8rtVWV_sQvqNHSTQl0NqcNvWm9Z8xLaDCn052iMeUKTfkNh5SJ2Vb0vaxdn2GjnfucnBRQWbzYzwF5u7tdTB-8p_n943Ty5AFPwsYTSmZKJgmXICGKOcRJkeVRFIBSqLIwEMBYJjESOVexH2NSMD-WjAOEKsvzYEDGXa4y2lqDRbp2x4HZppylO5ypw5k6nOkep3NcdY51m60w_9Mf-DnBdSfonK2p3QP_xv0CGQyCtw</recordid><startdate>20241206</startdate><enddate>20241206</enddate><creator>Mahale, Sachin D.</creator><creator>Yadav, Vinita</creator><creator>Gonnade, Rajesh G.</creator><creator>Mhaske, Santosh B.</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2841-0197</orcidid><orcidid>https://orcid.org/0000-0002-5859-0838</orcidid></search><sort><creationdate>20241206</creationdate><title>Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO t Bu-Mediated Cyclotrimerization of Aryl Vinyl Ketones</title><author>Mahale, Sachin D. ; Yadav, Vinita ; Gonnade, Rajesh G. ; Mhaske, Santosh B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a184t-5c9bc98819a9a671a78fbd663accecb435a00b9e65d1c727e8f027901aa4cbdd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mahale, Sachin D.</creatorcontrib><creatorcontrib>Yadav, Vinita</creatorcontrib><creatorcontrib>Gonnade, Rajesh G.</creatorcontrib><creatorcontrib>Mhaske, Santosh B.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mahale, Sachin D.</au><au>Yadav, Vinita</au><au>Gonnade, Rajesh G.</au><au>Mhaske, Santosh B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO t Bu-Mediated Cyclotrimerization of Aryl Vinyl Ketones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2024-12-06</date><risdate>2024</risdate><volume>89</volume><issue>23</issue><spage>17207</spage><epage>17212</epage><pages>17207-17212</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Herein, we disclose a simple one-pot method for an efficient regio- and stereoselective synthesis of 1,3,5-triaroylcyclohexanes from aryl vinyl ketones using potassium tert-butoxide. The developed protocol allows the construction of various symmetrically substituted cyclohexanes in good to excellent yields. The major product 2 also can be converted to the product 3 (all equatorial) conveniently by acid catalysis. This protocol features a good substrate scope and functional group compatibility.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>39535148</pmid><doi>10.1021/acs.joc.4c01695</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-2841-0197</orcidid><orcidid>https://orcid.org/0000-0002-5859-0838</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2024-12, Vol.89 (23), p.17207-17212
issn 0022-3263
1520-6904
language eng
recordid cdi_crossref_primary_10_1021_acs_joc_4c01695
source American Chemical Society Journals
title Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO t Bu-Mediated Cyclotrimerization of Aryl Vinyl Ketones
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-16T13%3A20%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Regio-%20and%20Stereoselective%20Construction%20of%201,3,5-Triaroylcyclohexanes%20via%20KO%20t%20Bu-Mediated%20Cyclotrimerization%20of%20Aryl%20Vinyl%20Ketones&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Mahale,%20Sachin%20D.&rft.date=2024-12-06&rft.volume=89&rft.issue=23&rft.spage=17207&rft.epage=17212&rft.pages=17207-17212&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.4c01695&rft_dat=%3Cacs_cross%3Eb612562526%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/39535148&rfr_iscdi=true