Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins
A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu( i ) initiated N-O bond cleavage, 1,5...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2021-04, Vol.57 (27), p.3379-3382 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Duan, Jindian Mao, Yiyang Xian, Anmei Rong, Binsen Xu, Gaochen Li, Zhenjiang Zhao, Lili Zhu, Ning Guo, Kai |
| description | A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(
i
) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.
A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. |
| doi_str_mv | 10.1039/d0cc07995b |
| format | Article |
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i
) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.
A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d0cc07995b</identifier><identifier>PMID: 33683244</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemical reactions ; Copper ; Crystallography ; Organic chemistry ; Oximes ; Regioselectivity ; Stereoselectivity ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2021-04, Vol.57 (27), p.3379-3382</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-3559c352460aecf522b17197cd376b2228330c4824ce914285c4a9b943c9a2293</citedby><cites>FETCH-LOGICAL-c337t-3559c352460aecf522b17197cd376b2228330c4824ce914285c4a9b943c9a2293</cites><orcidid>0000-0003-2580-6919 ; 0000-0002-1100-7297 ; 0000-0002-0013-3263</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33683244$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Duan, Jindian</creatorcontrib><creatorcontrib>Mao, Yiyang</creatorcontrib><creatorcontrib>Xian, Anmei</creatorcontrib><creatorcontrib>Rong, Binsen</creatorcontrib><creatorcontrib>Xu, Gaochen</creatorcontrib><creatorcontrib>Li, Zhenjiang</creatorcontrib><creatorcontrib>Zhao, Lili</creatorcontrib><creatorcontrib>Zhu, Ning</creatorcontrib><creatorcontrib>Guo, Kai</creatorcontrib><title>Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(
i
) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.
A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity.</description><subject>Chemical reactions</subject><subject>Copper</subject><subject>Crystallography</subject><subject>Organic chemistry</subject><subject>Oximes</subject><subject>Regioselectivity</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpd0U1LxDAQBuAgiuvXxbtS8CJKNc0kbXLU-gmCFwVBtKTZWa20zZqk6vrr7bq6grlMIM8MwxtCNhN6kFBQh0NqDM2UEuUCWUkg5bHg8m5xehcqzoCLAVn1_oX2JxFymQwAUgmM8xXymNvxGF1sdND15BOHkcOnynqs0YTqDaN72GcPkW7brtahsm1kR1Gja9vqgHHA8Iyub9JmUkf2o2rQR-9VeI4q3-vWr5Olka49bvzUNXJ7dnqTX8RX1-eX-dFVbACyEIMQyoBgPKUazUgwViZZojIzhCwtGWMSgBouGTeoEs6kMFyrUnEwSjOmYI3szuaOnX3t0IeiqbzButYt2s4XjCuppKR8Snf-0RfbubbfrmCCZjxjqUp7tTdTxlnvHY6Ksasa7SZFQotp6sUJzfPv1I97vP0zsisbHM7pb8w92JoB58389e_b4AuCWoVp</recordid><startdate>20210407</startdate><enddate>20210407</enddate><creator>Duan, Jindian</creator><creator>Mao, Yiyang</creator><creator>Xian, Anmei</creator><creator>Rong, Binsen</creator><creator>Xu, Gaochen</creator><creator>Li, Zhenjiang</creator><creator>Zhao, Lili</creator><creator>Zhu, Ning</creator><creator>Guo, Kai</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/0000-0003-2580-6919</orcidid><orcidid>https://orcid.org/0000-0002-1100-7297</orcidid><orcidid>https://orcid.org/0000-0002-0013-3263</orcidid></search><sort><creationdate>20210407</creationdate><title>Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins</title><author>Duan, Jindian ; Mao, Yiyang ; Xian, Anmei ; Rong, Binsen ; Xu, Gaochen ; Li, Zhenjiang ; Zhao, Lili ; Zhu, Ning ; Guo, Kai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-3559c352460aecf522b17197cd376b2228330c4824ce914285c4a9b943c9a2293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemical reactions</topic><topic>Copper</topic><topic>Crystallography</topic><topic>Organic chemistry</topic><topic>Oximes</topic><topic>Regioselectivity</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Duan, Jindian</creatorcontrib><creatorcontrib>Mao, Yiyang</creatorcontrib><creatorcontrib>Xian, Anmei</creatorcontrib><creatorcontrib>Rong, Binsen</creatorcontrib><creatorcontrib>Xu, Gaochen</creatorcontrib><creatorcontrib>Li, Zhenjiang</creatorcontrib><creatorcontrib>Zhao, Lili</creatorcontrib><creatorcontrib>Zhu, Ning</creatorcontrib><creatorcontrib>Guo, Kai</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>Duan, Jindian</au><au>Mao, Yiyang</au><au>Xian, Anmei</au><au>Rong, Binsen</au><au>Xu, Gaochen</au><au>Li, Zhenjiang</au><au>Zhao, Lili</au><au>Zhu, Ning</au><au>Guo, Kai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2021-04-07</date><risdate>2021</risdate><volume>57</volume><issue>27</issue><spage>3379</spage><epage>3382</epage><pages>3379-3382</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(
i
) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.
A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33683244</pmid><doi>10.1039/d0cc07995b</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-2580-6919</orcidid><orcidid>https://orcid.org/0000-0002-1100-7297</orcidid><orcidid>https://orcid.org/0000-0002-0013-3263</orcidid></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical reactions Copper Crystallography Organic chemistry Oximes Regioselectivity Stereoselectivity Substrates |
| title | Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins |
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