Acyl Transfer-Driven Rauhut–Currier Dimerization of Morita–Baylis–Hillman Ketones

Acyl Transfer-Driven Rauhut–Currier Dimerization of Morita–Baylis–Hillman Ketones

A serendipitous Rauhut–Currier dimerization of 1,1-disubstituted activated olefins derived from Morita–Baylis–Hillman adducts was observed in the presence of DABCO. The reaction is driven by the migration of an acyl group and produces multifunctionalized enol esters in yields greater than 90% in mos...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2023-02, Vol.88 (4), p.2023-2033
Hauptverfasser: Kumari, Rajkiran, Jha, Ajit Kumar, Goyal, Sophiya, Maan, Reena, Reddy, S. Rajagopala, Easwar, Srinivasan
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2033
container_issue 4
container_start_page 2023
container_title Journal of organic chemistry
container_volume 88
creator Kumari, Rajkiran
Jha, Ajit Kumar
Goyal, Sophiya
Maan, Reena
Reddy, S. Rajagopala
Easwar, Srinivasan
description A serendipitous Rauhut–Currier dimerization of 1,1-disubstituted activated olefins derived from Morita–Baylis–Hillman adducts was observed in the presence of DABCO. The reaction is driven by the migration of an acyl group and produces multifunctionalized enol esters in yields greater than 90% in most cases, without necessitating column chromatographic purification. The acyl transfer is thought to proceed via a transition state typical of a Morita–Baylis–Hillman (MBH) reaction, supported by a brief mechanistic study involving computational calculations.
doi_str_mv 10.1021/acs.joc.2c02244
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2774496886</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2774496886</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-845d13885d540bee63a832ce9dc9eb2b481b5a2a5ee02e5c2570925f606e2c3e3</originalsourceid><addsrcrecordid>eNp1kM9Kw0AQhxdRbK2evUmOgqTd7L8kx9qqFSuCVDyGzWaCW5Js3U2EevIdfEOfxJVUb85lhuGbH8yH0GmExxEm0UQqN14bNSYKE8LYHhpGnOBQpJjtoyH2y5ASQQfoyLk19sU5P0QDKmJOORVD9DxV2ypYWdm4Emw4t_oNmuBRdi9d-_XxOeus1WCDua7B6nfZatMEpgzujdWt9MCl3Fba-WGhq6qWTXAHrWnAHaODUlYOTnZ9hJ6ur1azRbh8uLmdTZehpJS2YcJ4EdEk4QVnOAcQVCaUKEgLlUJOcpZEOZdEcgBMgCvCY5wSXgosgCgKdITO-9yNNa8duDartVNQVbIB07mMxDFjqUgS4dFJjyprnLNQZhura2m3WYSzH5uZt5l5m9nOpr8424V3eQ3FH_-rzwMXPdBfdrbxv_4b9w1_NIMh</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2774496886</pqid></control><display><type>article</type><title>Acyl Transfer-Driven Rauhut–Currier Dimerization of Morita–Baylis–Hillman Ketones</title><source>American Chemical Society Journals</source><creator>Kumari, Rajkiran ; Jha, Ajit Kumar ; Goyal, Sophiya ; Maan, Reena ; Reddy, S. Rajagopala ; Easwar, Srinivasan</creator><creatorcontrib>Kumari, Rajkiran ; Jha, Ajit Kumar ; Goyal, Sophiya ; Maan, Reena ; Reddy, S. Rajagopala ; Easwar, Srinivasan</creatorcontrib><description>A serendipitous Rauhut–Currier dimerization of 1,1-disubstituted activated olefins derived from Morita–Baylis–Hillman adducts was observed in the presence of DABCO. The reaction is driven by the migration of an acyl group and produces multifunctionalized enol esters in yields greater than 90% in most cases, without necessitating column chromatographic purification. The acyl transfer is thought to proceed via a transition state typical of a Morita–Baylis–Hillman (MBH) reaction, supported by a brief mechanistic study involving computational calculations.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.2c02244</identifier><identifier>PMID: 36753536</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2023-02, Vol.88 (4), p.2023-2033</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-845d13885d540bee63a832ce9dc9eb2b481b5a2a5ee02e5c2570925f606e2c3e3</citedby><cites>FETCH-LOGICAL-a333t-845d13885d540bee63a832ce9dc9eb2b481b5a2a5ee02e5c2570925f606e2c3e3</cites><orcidid>0000-0002-7352-0897 ; 0000-0002-9835-010X</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.2c02244$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.2c02244$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36753536$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kumari, Rajkiran</creatorcontrib><creatorcontrib>Jha, Ajit Kumar</creatorcontrib><creatorcontrib>Goyal, Sophiya</creatorcontrib><creatorcontrib>Maan, Reena</creatorcontrib><creatorcontrib>Reddy, S. Rajagopala</creatorcontrib><creatorcontrib>Easwar, Srinivasan</creatorcontrib><title>Acyl Transfer-Driven Rauhut–Currier Dimerization of Morita–Baylis–Hillman Ketones</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A serendipitous Rauhut–Currier dimerization of 1,1-disubstituted activated olefins derived from Morita–Baylis–Hillman adducts was observed in the presence of DABCO. The reaction is driven by the migration of an acyl group and produces multifunctionalized enol esters in yields greater than 90% in most cases, without necessitating column chromatographic purification. The acyl transfer is thought to proceed via a transition state typical of a Morita–Baylis–Hillman (MBH) reaction, supported by a brief mechanistic study involving computational calculations.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kM9Kw0AQhxdRbK2evUmOgqTd7L8kx9qqFSuCVDyGzWaCW5Js3U2EevIdfEOfxJVUb85lhuGbH8yH0GmExxEm0UQqN14bNSYKE8LYHhpGnOBQpJjtoyH2y5ASQQfoyLk19sU5P0QDKmJOORVD9DxV2ypYWdm4Emw4t_oNmuBRdi9d-_XxOeus1WCDua7B6nfZatMEpgzujdWt9MCl3Fba-WGhq6qWTXAHrWnAHaODUlYOTnZ9hJ6ur1azRbh8uLmdTZehpJS2YcJ4EdEk4QVnOAcQVCaUKEgLlUJOcpZEOZdEcgBMgCvCY5wSXgosgCgKdITO-9yNNa8duDartVNQVbIB07mMxDFjqUgS4dFJjyprnLNQZhura2m3WYSzH5uZt5l5m9nOpr8424V3eQ3FH_-rzwMXPdBfdrbxv_4b9w1_NIMh</recordid><startdate>20230217</startdate><enddate>20230217</enddate><creator>Kumari, Rajkiran</creator><creator>Jha, Ajit Kumar</creator><creator>Goyal, Sophiya</creator><creator>Maan, Reena</creator><creator>Reddy, S. Rajagopala</creator><creator>Easwar, Srinivasan</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7352-0897</orcidid><orcidid>https://orcid.org/0000-0002-9835-010X</orcidid></search><sort><creationdate>20230217</creationdate><title>Acyl Transfer-Driven Rauhut–Currier Dimerization of Morita–Baylis–Hillman Ketones</title><author>Kumari, Rajkiran ; Jha, Ajit Kumar ; Goyal, Sophiya ; Maan, Reena ; Reddy, S. Rajagopala ; Easwar, Srinivasan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-845d13885d540bee63a832ce9dc9eb2b481b5a2a5ee02e5c2570925f606e2c3e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumari, Rajkiran</creatorcontrib><creatorcontrib>Jha, Ajit Kumar</creatorcontrib><creatorcontrib>Goyal, Sophiya</creatorcontrib><creatorcontrib>Maan, Reena</creatorcontrib><creatorcontrib>Reddy, S. Rajagopala</creatorcontrib><creatorcontrib>Easwar, Srinivasan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumari, Rajkiran</au><au>Jha, Ajit Kumar</au><au>Goyal, Sophiya</au><au>Maan, Reena</au><au>Reddy, S. Rajagopala</au><au>Easwar, Srinivasan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Acyl Transfer-Driven Rauhut–Currier Dimerization of Morita–Baylis–Hillman Ketones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2023-02-17</date><risdate>2023</risdate><volume>88</volume><issue>4</issue><spage>2023</spage><epage>2033</epage><pages>2023-2033</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A serendipitous Rauhut–Currier dimerization of 1,1-disubstituted activated olefins derived from Morita–Baylis–Hillman adducts was observed in the presence of DABCO. The reaction is driven by the migration of an acyl group and produces multifunctionalized enol esters in yields greater than 90% in most cases, without necessitating column chromatographic purification. The acyl transfer is thought to proceed via a transition state typical of a Morita–Baylis–Hillman (MBH) reaction, supported by a brief mechanistic study involving computational calculations.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>36753536</pmid><doi>10.1021/acs.joc.2c02244</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-7352-0897</orcidid><orcidid>https://orcid.org/0000-0002-9835-010X</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2023-02, Vol.88 (4), p.2023-2033
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2774496886
source American Chemical Society Journals
title Acyl Transfer-Driven Rauhut–Currier Dimerization of Morita–Baylis–Hillman Ketones
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-25T01%3A28%3A56IST&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=Acyl%20Transfer-Driven%20Rauhut%E2%80%93Currier%20Dimerization%20of%20Morita%E2%80%93Baylis%E2%80%93Hillman%20Ketones&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Kumari,%20Rajkiran&rft.date=2023-02-17&rft.volume=88&rft.issue=4&rft.spage=2023&rft.epage=2033&rft.pages=2023-2033&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.2c02244&rft_dat=%3Cproquest_cross%3E2774496886%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=2774496886&rft_id=info:pmid/36753536&rfr_iscdi=true