Enantioselective Intramolecular C−H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach
The first enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor‐ and donor/donor‐carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrof...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-07, Vol.55 (29), p.8452-8456 |
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| container_issue | 29 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Zhu, Dong Ma, Jun Luo, Kui Fu, Hongguang Zhang, Li Zhu, Shifa |
| description | The first enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor‐ and donor/donor‐carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee and 100 % atom efficiency.
Generous donor: Enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor and donor/donor carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee. |
| doi_str_mv | 10.1002/anie.201604211 |
| format | Article |
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Generous donor: Enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor and donor/donor carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201604211</identifier><identifier>PMID: 27265896</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>asymmetric catalysis ; Atom economy ; Carbenes ; Enantiomers ; heterocycles ; Insertion ; rhodium ; Tetrahydrofuran</subject><ispartof>Angewandte Chemie International Edition, 2016-07, Vol.55 (29), p.8452-8456</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5421-8c6ad9dda2a818b7ac059a61f2f36e1713ccc0f9f14428bc2ada7ae415f9dfa93</citedby><cites>FETCH-LOGICAL-c5421-8c6ad9dda2a818b7ac059a61f2f36e1713ccc0f9f14428bc2ada7ae415f9dfa93</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%2Fanie.201604211$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201604211$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27265896$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhu, Dong</creatorcontrib><creatorcontrib>Ma, Jun</creatorcontrib><creatorcontrib>Luo, Kui</creatorcontrib><creatorcontrib>Fu, Hongguang</creatorcontrib><creatorcontrib>Zhang, Li</creatorcontrib><creatorcontrib>Zhu, Shifa</creatorcontrib><title>Enantioselective Intramolecular C−H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>The first enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor‐ and donor/donor‐carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee and 100 % atom efficiency.
Generous donor: Enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor and donor/donor carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee.</description><subject>asymmetric catalysis</subject><subject>Atom economy</subject><subject>Carbenes</subject><subject>Enantiomers</subject><subject>heterocycles</subject><subject>Insertion</subject><subject>rhodium</subject><subject>Tetrahydrofuran</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkcuO0zAUhi0EYi6wZYkisWGTji-JL8sSOtNKo7IBwc46cWxNhtQudgKUJ2DNI_IkeJShQixAsuRzrO__j-0foWcELwjG9AJ8bxcUE44rSsgDdEpqSkomBHuY64qxUsianKCzlG4zLyXmj9EJFZTXUvFTdLPy4Mc-JDtYM_afbbHxY4RdyO00QCyan99_rPNhsjFjvgiueB18iAX4bq4u5r6B2FpvU9EeCii2wXc9fAvFcr-PAczNE_TIwZDs0_v9HL27XL1t1uX1m6tNs7wuTZ1fUErDoVNdBxQkka0Ag2sFnDjqGLdEEGaMwU45UlVUtoZCBwJsRWqnOgeKnaOXs28e-2myadS7Phk7DOBtmJImElNR4bwy-uIv9DZM0efbaaIwzz9E639T2YspzmWdqcVMmRhSitbpfex3EA-aYH2XlL5LSh-TyoLn97ZTu7PdEf8dTQbUDHzpB3v4j51ebjerP83LWdun0X49aiF-1FwwUev32yv9Ya3oq0ZILdkv6MGu5w</recordid><startdate>20160711</startdate><enddate>20160711</enddate><creator>Zhu, Dong</creator><creator>Ma, Jun</creator><creator>Luo, Kui</creator><creator>Fu, Hongguang</creator><creator>Zhang, Li</creator><creator>Zhu, Shifa</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160711</creationdate><title>Enantioselective Intramolecular C−H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach</title><author>Zhu, Dong ; Ma, Jun ; Luo, Kui ; Fu, Hongguang ; Zhang, Li ; Zhu, Shifa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5421-8c6ad9dda2a818b7ac059a61f2f36e1713ccc0f9f14428bc2ada7ae415f9dfa93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>asymmetric catalysis</topic><topic>Atom economy</topic><topic>Carbenes</topic><topic>Enantiomers</topic><topic>heterocycles</topic><topic>Insertion</topic><topic>rhodium</topic><topic>Tetrahydrofuran</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Dong</creatorcontrib><creatorcontrib>Ma, Jun</creatorcontrib><creatorcontrib>Luo, Kui</creatorcontrib><creatorcontrib>Fu, Hongguang</creatorcontrib><creatorcontrib>Zhang, Li</creatorcontrib><creatorcontrib>Zhu, Shifa</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Dong</au><au>Ma, Jun</au><au>Luo, Kui</au><au>Fu, Hongguang</au><au>Zhang, Li</au><au>Zhu, Shifa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Intramolecular C−H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-07-11</date><risdate>2016</risdate><volume>55</volume><issue>29</issue><spage>8452</spage><epage>8456</epage><pages>8452-8456</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>The first enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor‐ and donor/donor‐carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee and 100 % atom efficiency.
Generous donor: Enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor and donor/donor carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27265896</pmid><doi>10.1002/anie.201604211</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | asymmetric catalysis Atom economy Carbenes Enantiomers heterocycles Insertion rhodium Tetrahydrofuran |
| title | Enantioselective Intramolecular C−H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach |
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