Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes
The reactivity of donor‐acceptor (D‐A) cyclopropanes towards thioketenes was investigated. In a (3+2)‐cycloaddition using Sc(OTf)3 as a Lewis acidic catalyst, the corresponding exocyclic thioenol ethers (2‐methylidene tetrahydrothiophenes) were formed in moderate to good yields. Unsymmetrical thioke...
Gespeichert in:
| Veröffentlicht in: | European journal of organic chemistry 2021-12, Vol.2021 (46), p.6250-6253 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6253 |
|---|---|
| container_issue | 46 |
| container_start_page | 6250 |
| container_title | European journal of organic chemistry |
| container_volume | 2021 |
| creator | Mlostoń, Grzegorz Kowalczyk, Mateusz Augustin, André U. Jones, Peter G. Werz, Daniel B. |
| description | The reactivity of donor‐acceptor (D‐A) cyclopropanes towards thioketenes was investigated. In a (3+2)‐cycloaddition using Sc(OTf)3 as a Lewis acidic catalyst, the corresponding exocyclic thioenol ethers (2‐methylidene tetrahydrothiophenes) were formed in moderate to good yields. Unsymmetrical thioketenes provided E/Z mixtures at the double bond, with the Z isomer being preferred.
A series of dialkyl 2‐methylidene tetrahydrothiophene‐3,3‐dicarboxylates was prepared from (tert‐butyl)iso‐propyl thioketene via Lewis acid catalyzed (3+2)‐cycloaddition with D‐A cyclopropanes. In all studied cases the (Z)‐diastereoisomer was found as the main product. |
| doi_str_mv | 10.1002/ejoc.202100879 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9290834</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2694417261</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4689-9b142dcb199d838b38338d519b66a03110b1e931691d14332137bdc35e07495a3</originalsourceid><addsrcrecordid>eNqFkc1uEzEUhS0EoqWwZYlGYtMKTfC1PZ65G6QqLX-K1E2R2Fke2yEOk_HUnhCFFY_AM_IkOE0JPxtW177-7tE9PoQ8BToBStlLtwxmwijLl6bGe-QYKGJJJdL7-Sy4KAH5xyPyKKUlpRSlhIfkiFdNXTEpjkk7cxuffnz7fm68zWWqR91tvzpbnPIX7GzX2ZouaGv96EOfijAvLkIf4u2IccMYYnGLDDEMunep2PhxUVwvfPjsRpcbj8mDue6Se3JXT8iH15fX07fl7OrNu-n5rDRCNlhiC4JZ0wKibXjT8obzxlaArZSacgDagkMOEsFmY5wBr1treOVoLbDS_IS82usO63blrHH9GHWnhuhXOm5V0F79_dL7hfoUvihkSBsussDpnUAMN2uXRrXyybiuy7bCOikmUQiomYSMPv8HXYZ17LO9TOVfrjLJMjXZUyaGlKKbH5YBqnbxqV186hBfHnj2p4UD_iuvDOAe2PjObf8jpy7fX01_i_8EEvmqYw</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2609659442</pqid></control><display><type>article</type><title>Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Mlostoń, Grzegorz ; Kowalczyk, Mateusz ; Augustin, André U. ; Jones, Peter G. ; Werz, Daniel B.</creator><creatorcontrib>Mlostoń, Grzegorz ; Kowalczyk, Mateusz ; Augustin, André U. ; Jones, Peter G. ; Werz, Daniel B.</creatorcontrib><description>The reactivity of donor‐acceptor (D‐A) cyclopropanes towards thioketenes was investigated. In a (3+2)‐cycloaddition using Sc(OTf)3 as a Lewis acidic catalyst, the corresponding exocyclic thioenol ethers (2‐methylidene tetrahydrothiophenes) were formed in moderate to good yields. Unsymmetrical thioketenes provided E/Z mixtures at the double bond, with the Z isomer being preferred.
A series of dialkyl 2‐methylidene tetrahydrothiophene‐3,3‐dicarboxylates was prepared from (tert‐butyl)iso‐propyl thioketene via Lewis acid catalyzed (3+2)‐cycloaddition with D‐A cyclopropanes. In all studied cases the (Z)‐diastereoisomer was found as the main product.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100879</identifier><identifier>PMID: 35875264</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Communication ; Communications ; Cycloaddition ; Cyclopropane ; D-A cyclopropanes ; Ethers ; Lewis acids ; Organic compounds ; Sulfur heterocycles ; Thioketenes</subject><ispartof>European journal of organic chemistry, 2021-12, Vol.2021 (46), p.6250-6253</ispartof><rights>2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH</rights><rights>2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.</rights><rights>2021. This article is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4689-9b142dcb199d838b38338d519b66a03110b1e931691d14332137bdc35e07495a3</citedby><cites>FETCH-LOGICAL-c4689-9b142dcb199d838b38338d519b66a03110b1e931691d14332137bdc35e07495a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202100879$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202100879$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35875264$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mlostoń, Grzegorz</creatorcontrib><creatorcontrib>Kowalczyk, Mateusz</creatorcontrib><creatorcontrib>Augustin, André U.</creatorcontrib><creatorcontrib>Jones, Peter G.</creatorcontrib><creatorcontrib>Werz, Daniel B.</creatorcontrib><title>Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes</title><title>European journal of organic chemistry</title><addtitle>European J Org Chem</addtitle><description>The reactivity of donor‐acceptor (D‐A) cyclopropanes towards thioketenes was investigated. In a (3+2)‐cycloaddition using Sc(OTf)3 as a Lewis acidic catalyst, the corresponding exocyclic thioenol ethers (2‐methylidene tetrahydrothiophenes) were formed in moderate to good yields. Unsymmetrical thioketenes provided E/Z mixtures at the double bond, with the Z isomer being preferred.
A series of dialkyl 2‐methylidene tetrahydrothiophene‐3,3‐dicarboxylates was prepared from (tert‐butyl)iso‐propyl thioketene via Lewis acid catalyzed (3+2)‐cycloaddition with D‐A cyclopropanes. In all studied cases the (Z)‐diastereoisomer was found as the main product.</description><subject>Communication</subject><subject>Communications</subject><subject>Cycloaddition</subject><subject>Cyclopropane</subject><subject>D-A cyclopropanes</subject><subject>Ethers</subject><subject>Lewis acids</subject><subject>Organic compounds</subject><subject>Sulfur heterocycles</subject><subject>Thioketenes</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkc1uEzEUhS0EoqWwZYlGYtMKTfC1PZ65G6QqLX-K1E2R2Fke2yEOk_HUnhCFFY_AM_IkOE0JPxtW177-7tE9PoQ8BToBStlLtwxmwijLl6bGe-QYKGJJJdL7-Sy4KAH5xyPyKKUlpRSlhIfkiFdNXTEpjkk7cxuffnz7fm68zWWqR91tvzpbnPIX7GzX2ZouaGv96EOfijAvLkIf4u2IccMYYnGLDDEMunep2PhxUVwvfPjsRpcbj8mDue6Se3JXT8iH15fX07fl7OrNu-n5rDRCNlhiC4JZ0wKibXjT8obzxlaArZSacgDagkMOEsFmY5wBr1treOVoLbDS_IS82usO63blrHH9GHWnhuhXOm5V0F79_dL7hfoUvihkSBsussDpnUAMN2uXRrXyybiuy7bCOikmUQiomYSMPv8HXYZ17LO9TOVfrjLJMjXZUyaGlKKbH5YBqnbxqV186hBfHnj2p4UD_iuvDOAe2PjObf8jpy7fX01_i_8EEvmqYw</recordid><startdate>20211214</startdate><enddate>20211214</enddate><creator>Mlostoń, Grzegorz</creator><creator>Kowalczyk, Mateusz</creator><creator>Augustin, André U.</creator><creator>Jones, Peter G.</creator><creator>Werz, Daniel B.</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20211214</creationdate><title>Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes</title><author>Mlostoń, Grzegorz ; Kowalczyk, Mateusz ; Augustin, André U. ; Jones, Peter G. ; Werz, Daniel B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4689-9b142dcb199d838b38338d519b66a03110b1e931691d14332137bdc35e07495a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Communication</topic><topic>Communications</topic><topic>Cycloaddition</topic><topic>Cyclopropane</topic><topic>D-A cyclopropanes</topic><topic>Ethers</topic><topic>Lewis acids</topic><topic>Organic compounds</topic><topic>Sulfur heterocycles</topic><topic>Thioketenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mlostoń, Grzegorz</creatorcontrib><creatorcontrib>Kowalczyk, Mateusz</creatorcontrib><creatorcontrib>Augustin, André U.</creatorcontrib><creatorcontrib>Jones, Peter G.</creatorcontrib><creatorcontrib>Werz, Daniel B.</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mlostoń, Grzegorz</au><au>Kowalczyk, Mateusz</au><au>Augustin, André U.</au><au>Jones, Peter G.</au><au>Werz, Daniel B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>European J Org Chem</addtitle><date>2021-12-14</date><risdate>2021</risdate><volume>2021</volume><issue>46</issue><spage>6250</spage><epage>6253</epage><pages>6250-6253</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The reactivity of donor‐acceptor (D‐A) cyclopropanes towards thioketenes was investigated. In a (3+2)‐cycloaddition using Sc(OTf)3 as a Lewis acidic catalyst, the corresponding exocyclic thioenol ethers (2‐methylidene tetrahydrothiophenes) were formed in moderate to good yields. Unsymmetrical thioketenes provided E/Z mixtures at the double bond, with the Z isomer being preferred.
A series of dialkyl 2‐methylidene tetrahydrothiophene‐3,3‐dicarboxylates was prepared from (tert‐butyl)iso‐propyl thioketene via Lewis acid catalyzed (3+2)‐cycloaddition with D‐A cyclopropanes. In all studied cases the (Z)‐diastereoisomer was found as the main product.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35875264</pmid><doi>10.1002/ejoc.202100879</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1434-193X |
| ispartof | European journal of organic chemistry, 2021-12, Vol.2021 (46), p.6250-6253 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9290834 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Communication Communications Cycloaddition Cyclopropane D-A cyclopropanes Ethers Lewis acids Organic compounds Sulfur heterocycles Thioketenes |
| title | Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T22%3A33%3A52IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Lewis%E2%80%90Acid%E2%80%90Catalyzed%20(3+2)%E2%80%90Cycloadditions%20of%20Donor%E2%80%90Acceptor%20Cyclopropanes%20with%20Thioketenes&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Mlosto%C5%84,%20Grzegorz&rft.date=2021-12-14&rft.volume=2021&rft.issue=46&rft.spage=6250&rft.epage=6253&rft.pages=6250-6253&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.202100879&rft_dat=%3Cproquest_pubme%3E2694417261%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2609659442&rft_id=info:pmid/35875264&rfr_iscdi=true |