Heptamethylindenyl (Ind) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation
The diastereoselective coupling of -substituted arylhydroxamates and cyclopropenes mediated by Rh(iii) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2017, Vol.8 (2), p.1015-1020 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1020 |
|---|---|
| container_issue | 2 |
| container_start_page | 1015 |
| container_title | Chemical science (Cambridge) |
| container_volume | 8 |
| creator | Semakul, Natthawat Jackson, Kelvin E Paton, Robert S Rovis, Tomislav |
| description | The diastereoselective coupling of
-substituted arylhydroxamates and cyclopropenes mediated by Rh(iii) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the
-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[
]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules. |
| doi_str_mv | 10.1039/c6sc02587k |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_1893554212</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1884130068</sourcerecordid><originalsourceid>FETCH-LOGICAL-c477t-763d5931b45d1ca8b65f450463de76c84d3f529d4ea23fb00487e0dd4fb9da6c3</originalsourceid><addsrcrecordid>eNqFkUtr3DAUhUVpaUKSTX9A0XJScKOnH5tAMUknNFDoYy1k6bqjRJYcSzPF-fVxHh3aVe9Gl6vvHK50EHpHyUdKeHNmymQIk3V1-wodMiJoUUrevN73jBygk5RuyFKcU8mqt-iA1UJSxptD9HsNY9YD5M3sXbAQZo9XV8GeYgi685CwdTplmCAm8GCy2wHuINzrwVmdXQw49tjMxsdxiiOERbFzGn_brJxzp4XRWfv5HixuizXWj_on1TF602uf4OTlPEI_Ly9-tOvi-uvnq_bTdWFEVeWiKrmVDaedkJYaXXel7IUkYhlDVZpaWN5L1lgBmvG-I0TUFRBrRd81VpeGH6HzZ99x2w1gDYQ8aa_GyQ16mlXUTv17E9xG_Yo7JbkURFSLwerFYIp3W0hZDS4Z8F4HiNukaN1wKQVbvvP_aC0oJ6SsF_TDM2qmmNIE_X4jStRjrqotv7dPuX5Z4Pd_v2GP_kmRPwDyZ6BB</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1884130068</pqid></control><display><type>article</type><title>Heptamethylindenyl (Ind) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central Open Access</source><source>PubMed Central</source><creator>Semakul, Natthawat ; Jackson, Kelvin E ; Paton, Robert S ; Rovis, Tomislav</creator><creatorcontrib>Semakul, Natthawat ; Jackson, Kelvin E ; Paton, Robert S ; Rovis, Tomislav</creatorcontrib><description>The diastereoselective coupling of
-substituted arylhydroxamates and cyclopropenes mediated by Rh(iii) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the
-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[
]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c6sc02587k</identifier><identifier>PMID: 28451239</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Benzamide ; Chemical reactions ; Chemistry ; Coupling ; Esters ; Ligands ; Mathematical analysis ; Organic compounds ; Transformations</subject><ispartof>Chemical science (Cambridge), 2017, Vol.8 (2), p.1015-1020</ispartof><rights>This journal is © The Royal Society of Chemistry 2016 2016</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c477t-763d5931b45d1ca8b65f450463de76c84d3f529d4ea23fb00487e0dd4fb9da6c3</citedby><cites>FETCH-LOGICAL-c477t-763d5931b45d1ca8b65f450463de76c84d3f529d4ea23fb00487e0dd4fb9da6c3</cites><orcidid>0000-0002-0104-4166</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5354047/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5354047/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,725,778,782,862,883,4012,27906,27907,27908,53774,53776</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28451239$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Semakul, Natthawat</creatorcontrib><creatorcontrib>Jackson, Kelvin E</creatorcontrib><creatorcontrib>Paton, Robert S</creatorcontrib><creatorcontrib>Rovis, Tomislav</creatorcontrib><title>Heptamethylindenyl (Ind) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>The diastereoselective coupling of
-substituted arylhydroxamates and cyclopropenes mediated by Rh(iii) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the
-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[
]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules.</description><subject>Benzamide</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Coupling</subject><subject>Esters</subject><subject>Ligands</subject><subject>Mathematical analysis</subject><subject>Organic compounds</subject><subject>Transformations</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkUtr3DAUhUVpaUKSTX9A0XJScKOnH5tAMUknNFDoYy1k6bqjRJYcSzPF-fVxHh3aVe9Gl6vvHK50EHpHyUdKeHNmymQIk3V1-wodMiJoUUrevN73jBygk5RuyFKcU8mqt-iA1UJSxptD9HsNY9YD5M3sXbAQZo9XV8GeYgi685CwdTplmCAm8GCy2wHuINzrwVmdXQw49tjMxsdxiiOERbFzGn_brJxzp4XRWfv5HixuizXWj_on1TF602uf4OTlPEI_Ly9-tOvi-uvnq_bTdWFEVeWiKrmVDaedkJYaXXel7IUkYhlDVZpaWN5L1lgBmvG-I0TUFRBrRd81VpeGH6HzZ99x2w1gDYQ8aa_GyQ16mlXUTv17E9xG_Yo7JbkURFSLwerFYIp3W0hZDS4Z8F4HiNukaN1wKQVbvvP_aC0oJ6SsF_TDM2qmmNIE_X4jStRjrqotv7dPuX5Z4Pd_v2GP_kmRPwDyZ6BB</recordid><startdate>2017</startdate><enddate>2017</enddate><creator>Semakul, Natthawat</creator><creator>Jackson, Kelvin E</creator><creator>Paton, Robert S</creator><creator>Rovis, Tomislav</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-0104-4166</orcidid></search><sort><creationdate>2017</creationdate><title>Heptamethylindenyl (Ind) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation</title><author>Semakul, Natthawat ; Jackson, Kelvin E ; Paton, Robert S ; Rovis, Tomislav</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c477t-763d5931b45d1ca8b65f450463de76c84d3f529d4ea23fb00487e0dd4fb9da6c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Benzamide</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Coupling</topic><topic>Esters</topic><topic>Ligands</topic><topic>Mathematical analysis</topic><topic>Organic compounds</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Semakul, Natthawat</creatorcontrib><creatorcontrib>Jackson, Kelvin E</creatorcontrib><creatorcontrib>Paton, Robert S</creatorcontrib><creatorcontrib>Rovis, Tomislav</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Semakul, Natthawat</au><au>Jackson, Kelvin E</au><au>Paton, Robert S</au><au>Rovis, Tomislav</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Heptamethylindenyl (Ind) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2017</date><risdate>2017</risdate><volume>8</volume><issue>2</issue><spage>1015</spage><epage>1020</epage><pages>1015-1020</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>The diastereoselective coupling of
-substituted arylhydroxamates and cyclopropenes mediated by Rh(iii) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the
-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[
]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>28451239</pmid><doi>10.1039/c6sc02587k</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-0104-4166</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2017, Vol.8 (2), p.1015-1020 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1893554212 |
| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Benzamide Chemical reactions Chemistry Coupling Esters Ligands Mathematical analysis Organic compounds Transformations |
| title | Heptamethylindenyl (Ind) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T19%3A38%3A29IST&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=Heptamethylindenyl%20(Ind)%20enables%20diastereoselective%20benzamidation%20of%20cyclopropenes%20via%20Rh(iii)-catalyzed%20C-H%20activation&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Semakul,%20Natthawat&rft.date=2017&rft.volume=8&rft.issue=2&rft.spage=1015&rft.epage=1020&rft.pages=1015-1020&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/c6sc02587k&rft_dat=%3Cproquest_pubme%3E1884130068%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=1884130068&rft_id=info:pmid/28451239&rfr_iscdi=true |